Abstract
The review covers the state of the art in methods of synthesis of acyclic geminal bis-peroxides, including bis-hydroperoxides, bis(1-hydroperoxyalkyl) peroxides, and 1-hydroperoxyalkyl 1-hydroxyalkyl peroxides. Most attention has been paid to the literature since 2000. This period of time is characterized by studies of mechanisms of formation of peroxides and hence by the development of effective and scalable procedures for the synthesis of acyclic geminal bis-peroxides via reactions of carbonyl compounds, ketals, and enol ethers with hydrogen peroxide and hydroperoxides in media that are uncommon for this field of chemistry. These procedures made it possible to extend the scope of application of acyclic geminal bis-peroxides in materials chemistry as initiators of radical polymerization and cross-linking.
Similar content being viewed by others
REFERENCES
Zhou, W.-S. and Xu, X.-X., Acc. Chem. Res., 1994, vol. 27, p. 211. https://doi.org/10.1021/ar00043a005
White, N.J., Science, 2008, vol. 320, p. 330. https://doi.org/10.1126/science.1155165
Haynes, R.K. and Vonwiller, S.C., Acc. Chem. Res., 1997, vol. 30, p. 73. https://doi.org/10.1021/ar950058w
Kumar, V., Mahajan, A., and Chibale, K., Bioorg. Med. Chem., 2009, vol. 17, p. 2236. https://doi.org/10.1016/j.bmc.2008.10.072
Meshnick, S.R., Jefford, C.W., Posner, G.H., Avery, M.A., and Peters, W., Parasitol. Today, 1996, vol. 12, p. 79. https://doi.org/10.1016/0169-4758(96)80660-0
Vil’, V.A., Yaremenko, I.A., Ilovaisky, A.I., and Terent’ev, A.O., Molecules, 2017, vol. 22, p. 117. https://doi.org/10.3390/molecules22010117
Tang, Y., Dong, Y., and Vennerstrom, J.L., Med. Res. Rev., 2004, vol. 24, p. 425. https://doi.org/10.1002/med.10066
Jefford, C.W., Drug Discovery Today, 2007, vol. 12, p. 487. https://doi.org/10.1016/j.drudis.2007.04.009
Opsenica, D.M. and Šolaja, B.A., J. Serb. Chem. Soc., 2009, vol. 74, p. 1155. https://doi.org/10.2298/JSC0911155O
Dembitsky, V.M., Eur. J. Med. Chem., 2008, vol. 43, p. 223. https://doi.org/10.1016/j.ejmech.2007.04.019
Chaturvedi, D., Goswami, A., Pratim Saikia, P., Barua, N.C., and Rao, P.G., Chem. Soc. Rev., 2010, vol. 39, p. 435. https://doi.org/10.1039/B816679J
Liu, D.-Z. and Liu, J.-K., Nat. Prod. Bioprospect., 2013, vol. 3, p. 161. https://doi.org/10.1007/s13659-013-0042-7
Yaremenko, I.A., Coghi, P., Prommana, P., Qiu, C., Radulov, P.S., Qu, Y., Belyakova, Y.Y., Zanforlin, E., Kokorekin, V.A., Wu, Y.Y.J., Fleury, F., Uthaipibull, C., Wong, V.K.W., and Terent’ev, A.O., ChemMedChem, 2020, vol. 15, p. 1118. https://doi.org/10.1002/cmdc.202000042
Vil’, V.A., Yaremenko, I.A., Fomenkov, D.I., Levitsky, D.O., Fleury, F., and Terent’ev, A.O., Chem. Heterocycl. Compd., 2020, vol. 56, p. 722. https://doi.org/10.1007/s10593-020-02722-4
Coghi, P., Yaremenko, I.A., Prommana, P., Radulov, P.S., Syroeshkin, M.A., Wu, Y.J., Gao, J.Y., Gordillo, F.M., Mok, S., Wong, V.K.W., Uthaipibull, C., and Terent’ev, A.O., ChemMedChem, 2018, vol. 13, p. 902. https://doi.org/10.1002/cmdc.201700804
Yaremenko, I.A., Syroeshkin, M.A., Levitsky, D.O., Fleury, F., and Terent’ev, A.O., Med. Chem. Res., 2017, vol. 26, p. 170. https://doi.org/10.1007/s00044-016-1736-2
Keiser, J. and Utzinger, J., Trends Parasitol., 2007, vol. 23, p. 555. https://doi.org/10.1016/j.pt.2007.07.012
Muraleedharan, K.M. and Avery, M.A., Drug Discovery Today, 2009, vol. 14, p. 793. https://doi.org/10.1016/j.drudis.2009.05.008
Panic, G., Duthaler, U., Speich, B., and Keiser, J., Int. J. Parasitol.: Drugs Drug Resist., 2014, vol. 4, p. 185. https://doi.org/10.1016/j.ijpddr.2014.07.002
Cowan, N., Yaremenko, I.A., Krylov, I.B., Terent’ev, A.O., and Keiser, J., Bioorg. Med. Chem., 2015, vol. 23, p. 5175. https://doi.org/10.1016/j.bmc.2015.02.010
Ingram, K., Yaremenko, I.A., Krylov, I.B., Hofer, L., Terent’ev, A.O., and Keiser, J., J. Med. Chem., 2012, vol. 55, p. 8700. https://doi.org/10.1021/jm3009184
Efferth, T., Marschall, M., Wang, X., Huong, S.-M., Hauber, I., Olbrich, A., Kronschnabl, M., Stamminger, T., and Huang, E.-S., J. Mol. Med., 2002, vol. 80, p. 233. https://doi.org/10.1007/s00109-001-0300-8
Efferth, T., Romero, M.R., Wolf, D.G., Stamminger, T., Marin, J.J.G., and Marschall, M., Clin. Infect. Dis., 2008, vol. 47, p. 804. https://doi.org/10.1086/591195
Jia, M., Zhao, R., Xu, B., Yan, W., Chu, F., Gu, H., Xie, T., Xiang, H., Ren, J., Chen, D., Wang, P., and Lei, H., MedChemComm., 2017, vol. 8, p. 148. https://doi.org/10.1039/C6MD00344C
Vil’, A.V., Yaremenko, A.I., Ilovaisky, I.A., and Terent’ev, O.A., Molecules, 2017, vol. 22, article no. 1881. https://doi.org/10.3390/molecules22111881
Yaremenko, I.A., Radulov, P.S., Belyakova, Y.Y., Demina, A.A., Fomenkov, D.I., Barsukov, D.V., Subbotina, I.R., Fleury, F., and Terent’ev, A.O., Chem. Eur. J., 2020, vol. 26, p. 4734. https://doi.org/10.1002/chem.201904555
Yaremenko, I.A., Syromyatnikov, M.Y., Radulov, P.S., Belyakova, Y.Y., Fomenkov, D.I., Popov, V.N., and Terent’ev, A.O., Molecules, 2020, vol. 25, article no. 1954. https://doi.org/10.3390/molecules25081954
Kitis, M., Environ. Int., 2004, vol. 30, p. 47. https://doi.org/10.1016/S0160-4120(03)00147-8
Chassot, A.L.C., Poisl, M.I.P., and Samuel, S.M.W., Braz. Dent. J., 2006, vol. 17, p. 117. https://doi.org/10.1590/S0103-64402006000200006
Baldry, M.G.C. and French, M.S., Water Sci. Technol., 1989, vol. 21, p. 203. https://doi.org/10.2166/wst.1989.0100
Alvaro, J.E., Moreno, S., Dianez, F., Santos, M., Carrasco, G., and Urrestarazu, M., J. Food Eng., 2009, vol. 95, p. 11. https://doi.org/10.1016/j.jfoodeng.2009.05.003
Luukkonen, T. and Pehkonen, S.O., Crit. Rev. Environ. Sci. Technol., 2017, vol. 47, p. 1. https://doi.org/10.1080/10643389.2016.1272343
Tropina, V.I., Krivykh, O.V., Sadchikova, N.P., Terent’ev, A.O., and Krylov, I.B., Pharm. Chem. J., 2010, vol. 44, p. 248. https://doi.org/10.1007/s11094-010-0441-6
Wu, X.-F., Gong, J.-L., and Qi, X., Org. Biomol. Chem., 2014, vol. 12, p. 5807. https://doi.org/10.1039/C4OB00276H
Schmidt, R.J., Appl. Catal., A, 2005, vol. 280, p. 89. https://doi.org/10.1016/j.apcata.2004.08.030
Zhu, Y., Wang, Q., Cornwall, R.G., and Shi, Y., Chem. Rev., 2014, vol. 114, p. 8199. https://doi.org/10.1021/cr500064w
Fisher, T.J. and Dussault, P.H., Tetrahedron, 2017, vol. 73, p. 4233. https://doi.org/10.1016/j.tet.2017.03.039
Vil’, V.A., Gorlov, E.S., Bityukov, O.V., Barsegyan, Y.A., Romanova, Y.E., Merkulova, V.M., and Terent’ev, A.O., Adv. Synth. Catal., 2019, vol. 361, p. 3173. https://doi.org/10.1002/adsc.201900271
Barsegyan, Y.A. and Vil’, V.A., Chem. Heterocycl. Compd., 2019, vol. 55, p. 1035. https://doi.org/10.1007/s10593-019-02572-9
Gaylord, N.G., Mandal, B.M., and Martan, M., J. Polym. Sci., Polym. Lett. Ed., 1976, vol. 14, p. 555. https://doi.org/10.1002/pol.1976.130140908
Emami, S.H., Salovey, R., and Hogen-Esch, T.E., J. Polym. Sci., Part A: Polym. Chem., 2002, vol. 40, p. 3021. https://doi.org/10.1002/pola.10367
Russell, K.E., Prog. Polym. Sci., 2002, vol. 27, p. 1007. https://doi.org/10.1016/S0079-6700(02)00007-2
Islamova, R.M., Ishkinina, O.I., Nazarova, S.V., Chupakhin, O.N., Utepova, I.A., Andriyashina, N.M., and Terent’ev, A.O., Russ. Chem. Bull., Int. Ed., 2013, vol. 62, p. 1282. https://doi.org/10.1007/s11172-013-0177-z
Klapötke, T.M. and Wloka, T., Patai’s Chemistry of Functional Groups, Hoboken: Wiley, 2009, p. 1. https://doi.org/10.1002/9780470682531.pat0879
Flory, P.J., Principles of Polymer Chemistry, New York: Cornell Univ. Press, 1953.
Antonovskii, V.L., Organicheskie perekisnye initsiatory (Organic Peroxide Initiators), Moscow: Khimiya, 1972.
Antonovskii, V.L. and Khursan, S.L., Fizicheskaya khimiya organicheskikh peroksidov (Physical Chemistry of Organic Peroxides), Moscow: Akademkniga, 2003.
Rakhimov, A.I., Khimiya i tekhnologiya organicheskikh perekisnykh soedinenii (Chemistry and Technology of Organic Peroxy Compounds), Moscow: Khimiya, 1979.
Swern, D., Organic Peroxides, New York: Wiley, 1970.
The Chemistry of Peroxides, Liebman, F., Greer, A., Rappoport, Z., Marek, I., and Patai, S., Eds., Hoboken: Wiley, 2015, vol. 3.
Schulz, M., Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer, Adam, W., Ed., Weinheim: Wiley-VCH, 2000, p. 1. https://doi.org/10.1002/3527600396.ch1
Vil’, V.A., Gomes, G.d.P., Ekimova, M.V., Lyssenko, K.A., Syroeshkin, M.A., Nikishin, G.I., Alabugin, I.V., and Terent’ev, A.O., J. Org. Chem., 2018, vol. 83, p. 13427. https://doi.org/10.1021/acs.joc.8b02218
Denisov, E.T., Denisova, T.G., and Pokidova, T.S., Handbook of Free Radical Initiators, Hoboken: Wiley, 2005, p. 61. https://doi.org/10.1002/0471721476.ch4
Denisov, E.T., Denisova, T.G., and Pokidova, T.S., Handbook of Free Radical Initiators, Hoboken: Wiley, 2005, p. 129. https://doi.org/10.1002/0471721476.ch5
Sheppard, C.S. and Kamath, V.R., Polym. Eng. Sci., 1979, vol. 19, p. 597. https://doi.org/10.1002/pen.760190902
Handbook of Vinyl Polymers: Radical Polymerization, Process, and Technology, Mishra, M. and Yagci, Y., Eds., Boca Raton: CRC Press, 2016, 2nd ed.
Terent’ev, A.O., Platonov, M.M., Tursina, A.I., Chernyshev, V.V., and Nikishin, G.I., J. Org. Chem., 2008, vol. 73, p. 3169. https://doi.org/10.1021/jo7027213
Luft, G., Bitsch, H., and Seidl, H., J. Macromol. Sci., Part A: Chem., 1977, vol. 11, p. 1089. https://doi.org/10.1080/00222337708061313
Lowell, A.I. and Price, J.R., J. Polym. Sci., 1960, vol. 43, p. 1. https://doi.org/10.1002/pol.1960.1204314101
Li, X., Koseki, H., Iwata, Y., and Mok, Y.-S., J. Loss Prev. Process Ind., 2004, vol. 17, p. 23. https://doi.org/10.1016/j.jlp.2003.08.003
Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer, Adam, W., Ed., Weinheim: Wiley-VCH, 2000. https://doi.org/10.1002/3527600396
Schwartz C. and Dussault, P.H., Patai’s Chemistry of Functional Groups, Hoboken: Wiley, 2009, p. 1. https://doi.org/10.1002/9780470682531.pat0871
van Tonder, J.H., Synlett, 2014, vol. 25, p. 1629. https://doi.org/10.1055/s-0034-1378210
Kropf, H., Methoden der Organischen Chemie (Houben-Weyl), 1988.
Zmitek, K., Zupan, M., and Iskra, J., Org. Biomol. Chem., 2007, vol. 5, p. 3895. https://doi.org/10.1039/B711647K
Gandhi, H., O’Reilly, K., Gupta, M.K., Horgan, C., O’Leary, E.M., and O’Sullivan, T.P., RSC Adv., 2017, vol. 7, p. 19506. https://doi.org/10.1039/C6RA28489B
McCullough, K.J., Morgan, A.R., Nonhebel, D.C., Pauson, P.L., and White, G.J., J. Chem. Res., Miniprint, 1980, p. 601.
Cubbon, R.C.P. and Hewlett, C., J. Chem. Soc. C, 1968, p. 2986. https://doi.org/10.1039/J39680002986
Jefford, C.W., Li, Y., Jaber, A., and Boukouvalas, J., Synth. Commun., 1990, vol. 20, p. 2589. https://doi.org/10.1080/00397919008051466
Li, Y., Hao, H.-D., Zhang, Q., and Wu, Y., Org. Lett., 2009, vol. 11, p. 1615. https://doi.org/10.1021/ol900262t
Terent’ev, A.O., Kutkin, A.V., Platonov, M.M., Ogibin, Y.N., and Nikishin, G.I., Tetrahedron Lett., 2003, vol. 44, p. 7359. https://doi.org/10.1016/S0040-4039(03)01844-6
Terent’ev, A.O., Kutkin, A.V., Platonov, M.M., Vorontsov, I.I., Antipin, M.Y., Ogibin, Y.N., and Nikishin, G.I., Russ. Chem. Bull., Int. Ed., 2004, vol. 53, p. 681. https://doi.org/10.1023/B:RUCB.0000035657.58776.cc
Wittig, G. and Pieper, G., Ber. Dtsch. Chem. Ges., 1940, vol. 73, p. 295. https://doi.org/10.1002/cber.19400730402
Criegee, R., Schnorrenberg, W., and Becke, J., Justus Liebigs Ann. Chem., 1949, vol. 565, p. 7. https://doi.org/10.1002/jlac.19495650103
Criegee, R., Pilz, H., and Flygare, H., Ber. Dtsch. Chem. Ges., 1939, vol. 72, p. 1799. https://doi.org/10.1002/cber.19390720926
Criegee, R. and Dietrich, H., Justus Liebigs Ann. Chem., 1948, vol. 560, p. 135. https://doi.org/10.1002/jlac.19485600107
Wooding, N.S., Higginson, W.C.E., Cooper, W., Davison, W.H.T., Cocker, W., Cross, B.E., McCormick, J., Pelletier, S.W., Josey, A.D., Bauer, L., Baxter, J.N., Cymerman, J., Sheldon, W.J., Dawson, J.K., Astell-Burt, A., Hammick, D.L., Curtis, R.G., Silberman, H., and Bryan, J.D., J. Chem. Soc., 1952, p. 1178. https://doi.org/10.1039/JR9520001178
Kharasch, M.S. and Sosnovsky, G., J. Org. Chem., 1958, vol. 23, p. 1322. https://doi.org/10.1021/jo01103a021
Brown, N., Hartig, M.J., Roedel, M.J., Anderson, A.W., and Schweitzer, C.E., J. Am. Chem. Soc., 1955, vol. 77, p. 1756. https://doi.org/10.1021/ja01612a010
Zorn, H., Till, H., and Mitterhofer, F., Monatsh Chem., 1965, vol. 96, p. 430. https://doi.org/10.1007/BF00909451
Milas, N.A. and Belič, I., J. Am. Chem. Soc., 1959, vol. 81, p. 3358. https://doi.org/10.1021/ja01522a050
Warnant, J., Jofy, R., Muthieu, J., and Velluz, L., Bull. Soc. Chim. Fr., 1957, p. 331.
Velluz, L., Amiard, G., Martel, J., and Warnant, J., Bull. Soc. Chim. Fr., 1957, p. 879.
Cosijn, A.H.M. and Ossewold, M.G.J., Recl. Trav. Chim. Pays–Bas, 1968, vol. 87, p. 1264. https://doi.org/10.1002/recl.19680871108
Milas, N.A. and Golubović, A., J. Am. Chem. Soc., 1959, vol. 81, p. 6461. https://doi.org/10.1021/ja01533a033
Milas, N.A. and Golubović, A., J. Am. Chem. Soc., 1959, vol. 81, p. 5824. https://doi.org/10.1021/ja01530a068
Ferrari, C.G. and Kazuo, H., US Patent no. 3047406A, 1962.
Groth, P., Acta Chem. Scand., Ser. A, 1975, vol. 29, p. 840. https://doi.org/10.3891/acta.chem.scand.29a-0840
Kim, H.-S., Nagai, Y., Ono, K., Begum, K., Wataya, Y., Hamada, Y., Tsuchiya, K., Masuyama, A., Nojima, M., and McCullough, K.J., J. Med. Chem., 2001, vol. 44, p. 2357. https://doi.org/10.1021/jm010026g
Ledaal, T.S.T., Acta Chem. Scand., 1967, vol. 21, p. 1658. https://doi.org/10.3891/acta.chem.scand.21-1658
Dåshes, T.L.T., Acta Chem. Scand., 1971, vol. 25, p. 1906. https://doi.org/10.3891/acta.chem.scand.25-1906
Ramirez, A. and Woerpel, K.A., Org. Lett., 2005, vol. 7, p. 4617. https://doi.org/10.1021/ol051703u
Nagahama, S., Kobayashi, H., and Akiyoshi, S., Bull. Chem. Soc. Jpn., 1959, vol. 32, p. 366. https://doi.org/10.1246/bcsj.32.366
Terent’ev, A.O., Platonov, M.M., Ogibin, Y.N., and Nikishin, G.I., Synth. Commun., 2007, vol. 37, p. 1281. https://doi.org/10.1080/00397910701226384
Todorović, N.M., Stefanovic, M., Tinant, B., Declercq, J.-P., Makler, M.T., and S̆olaja, B.A., Steroids, 1996, vol. 61, p. 688. https://doi.org/10.1016/S0039-128X(96)00203-6
Šolaja, B.A., Terzić, N., Pocsfalvi, G., Gerena, L., Tinant, B., Opsenica, D., and Milhous, W.K., J. Med. Chem., 2002, vol. 45, p. 3331. https://doi.org/10.1021/jm020891g
Kumawat, M.K., Parida, P., and Chetia, D., Med. Chem. Res., 2016, vol. 25, p. 1993. https://doi.org/10.1007/s00044-016-1644-5
Khosravi, K., Pirbodaghi, F., Kazemi, S., and Asgari, A., J. Iran. Chem. Soc., 2015, vol. 12, p. 1333. https://doi.org/10.1007/s13738-015-0598-8
Bunge, A., Hamann, H.-J., and Liebscher, J., Tetrahedron Lett., 2009, vol. 50, p. 524. https://doi.org/10.1016/j.tetlet.2008.11.055
Terent’ev, A.O., Platonov, M.M., Kashin, A.S., and Nikishin, G.I., Tetrahedron, 2008, vol. 64, p. 7944. https://doi.org/10.1016/j.tet.2008.06.027
Vil’, V.A., Gomes, G.d.P., Bityukov, O.V., Lyssenko, K.A., Nikishin, G.I., Alabugin, I.V., and Terent’ev, A.O., Angew. Chem., Int. Ed., 2018, vol. 57, p. 3372. https://doi.org/10.1002/anie.201712651
Terent’ev, A., Platonov, M., and Kutkin, A., Open Chem., 2006, vol. 4, p. 207. https://doi.org/10.2478/s11532-006-0012-6
Vil’, V.A., Barsegyan, Y.A., Kuhn, L., Ekimova, M.V., Semenov, E.A., Korlyukov, A.A., Terent’ev, A.O., and Alabugin, I.V., Chem. Sci., 2020, vol. 11, p. 5313. https://doi.org/10.1039/D0SC01025A
Das, B., Veeranjaneyulu, B., Krishnaiah, M., and Balasubramanyam, P., J. Mol. Catal. A: Chem., 2008, vol. 284, p. 116. https://doi.org/10.1016/j.molcata.2008.01.016
Azarifar, D., Najminejad, Z., and Khosravi, K., Synth. Commun., 2013, vol. 43, p. 826. https://doi.org/10.1080/00397911.2011.610549
Surya Prakash, G.K., Shakhmin, A., Glinton, K.E., Rao, S., Mathew, T., and Olah, G.A., Green Chem., 2014, vol. 16, p. 3616. https://doi.org/10.1039/C4GC00586D
Azarifar, D., Khosravi, K., and Soleimanei, F., Molecules, 2010, vol. 15, p. 1433. https://doi.org/10.3390/molecules15031433
Yan, X., Chen, J., Zhu, Y.-T., and Qiao, C., Synlett, 2011, vol. 2011, p. 2827. https://doi.org/10.1055/s-0031-1289864
Khosravi, K. and Kazemi, S., J. Chin. Chem. Soc., 2012, vol. 59, p. 641. https://doi.org/10.1002/jccs.201100605
Iskra, J., Bonnet-Delpon, D., and Bégué, J.-P., Tetrahedron Lett., 2003, vol. 44, p. 6309. https://doi.org/10.1016/S0040-4039(03)01472-2
Ghorai, P. and Dussault, P.H., Org. Lett., 2008, vol. 10, p. 4577. https://doi.org/10.1021/ol801859c
Hang, J., Ghorai, P., Finkenstaedt-Quinn, S.A., Findik, I., Sliz, E., Kuwata, K.T., and Dussault, P.H., J. Org. Chem., 2012, vol. 77, p. 1233. https://doi.org/10.1021/jo202265j
Azarifar, D., Khosravi, K., and Soleimanei, F., Synthesis, 2009, vol. 2009, p. 2553. https://doi.org/10.1055/s-0029-1217394
Azarifar, D. and Khosravi, K., J. Iran. Chem. Soc., 2011, vol. 8, p. 1006. https://doi.org/10.1007/BF03246556
Sashidhara, K.V., Avula, S.R., Ravithej Singh, L., and Palnati, G.R., Tetrahedron Lett., 2012, vol. 53, p. 4880. https://doi.org/10.1016/j.tetlet.2012.07.001
Žmitek, K., Zupan, M., Stavber, S., and Iskra, J., Org. Lett., 2006, vol. 8, p. 2491. https://doi.org/10.1021/ol060590r
Žmitek, K., Zupan, M., Stavber, S., and Iskra, J., J. Org. Chem., 2007, vol. 72, p. 6534. https://doi.org/10.1021/jo0708745
Zhang, Q., Li, Y., and Wu, Y.-K., Chin. J. Chem., 2007, vol. 25, p. 1304. https://doi.org/10.1002/cjoc.200790242
Das, B., Krishnaiah, M., Veeranjaneyulu, B., and Ravikanth, B., Tetrahedron Lett., 2007, vol. 48, p. 6286. https://doi.org/10.1016/j.tetlet.2007.07.012
Radulov, P.S. and Vil’, V.A., Chem. Heterocycl. Compd., 2020, vol. 56, p. 299. https://doi.org/10.1007/s10593-020-02657-w
Khosravi, K., Zendehdel, M., Naserifar, S., Tavakoli, F., Khalaji, K., and Asgari, A., J. Chem. Res., 2016, vol. 40, p. 744. https://doi.org/10.3184/174751916X14792244600532
Do, S.-H., Batchelor, B., Lee, H.-K., and Kong, S.-H., Chemosphere, 2009, vol. 75, p. 8. https://doi.org/10.1016/j.chemosphere.2008.11.075
Hasan, M.A., Zaki, M.I., Pasupulety, L., and Kumari, K., Appl. Catal., A, 1999, vol. 181, p. 171. https://doi.org/10.1016/S0926-860X(98)00430-X
Yang, Y., Tseung, A.C.C., and Lin, Z.G., J. Electroanal. Chem., 1994, vol. 370, p. 159. https://doi.org/10.1016/0022-0728(94)03201-7
Masuyama, A., Sugawara, T., Nojima, M., and McCullough, K.J., Tetrahedron, 2003, vol. 59, p. 353. https://doi.org/10.1016/S0040-4020(02)01522-3
Lempers, H.E.B., Sheldon, R.A., and Swift, K.A.D., Chem. Lett., 2002, vol. 31, p. 830. https://doi.org/10.1246/cl.2002.830
Ogibin, Y.N., Terent’ev, A.O., Ananikov, V.P., and Nikishin, G.I., Russ. Chem. Bull., Int. Ed., 2001, vol. 50, p. 2149. https://doi.org/10.1023/A:1015009603719
Blank, O., Raschke, N., and Heinrich, M.R., Tetrahedron Lett., 2010, vol. 51, p. 1758. https://doi.org/10.1016/j.tetlet.2010.01.098
Prechter, A. and Heinrich, M.R., Synthesis, 2011, vol. 2011, p. 1515. https://doi.org/10.1055/s-0030-1260006
Ogibin, Y.N., Starostin, E.K., Aleksandrov, A.V., Pivnitsky, K.K., and Nikishin, G.I., Synthesis, 1994, vol. 1994, p. 901. https://doi.org/10.1055/s-1994-25596
Liu, Y.-H., Deng, J., Gao, J.-W., and Zhang, Z.-H., Adv. Synth. Catal., 2012, vol. 354, p. 441. https://doi.org/10.1002/adsc.201100561
Terent’ev, A.O., Khodykin, S.V., Krylov, I.B., Ogibin, Y.N., and Nikishin, G.I., Synthesis, 2006, vol. 2006, p. 1087. https://doi.org/10.1055/s-2006-926386
Terent’ev, A.O., Borisov, D.A., Krylov, I.B., and Nikishin, G.I., Synth. Commun., 2007, vol. 37, p. 3151. https://doi.org/10.1080/00397910701545171
Nikishin, G.I., Kapustina, N.I., Sokova, L.L., Bityukov, O.V., and Terent’ev, A.O., Tetrahedron Lett., 2020, vol. 61, article ID 152154. https://doi.org/10.1016/j.tetlet.2020.152154
Pettinari, C., Marchetti, F., Cingolani, A., Drozdov, A., and Troyanov, S., Chem. Commun., 2000, p. 1901. https://doi.org/10.1039/B005221N
Tada, N., Cui, L., Okubo, H., Miura, T., and Itoh, A., Adv. Synth. Catal., 2010, vol. 352, p. 2383. https://doi.org/10.1002/adsc.201000357
Cui, L., Tada, N., Okubo, H., Miura, T., and Itoh, A., Green Chem., 2011, vol. 13, p. 2347. https://doi.org/10.1039/C1GC15437K
Tada, N., Cui, L., Okubo, H., Miura, T., and Itoh, A., Chem. Commun., 2010, vol. 46, p. 1772. https://doi.org/10.1039/B917056A
Starkl Renar, K., Pecar, S., and Iskra, J., Org. Biomol. Chem., 2015, vol. 13, p. 9369. https://doi.org/10.1039/C5OB01503K
Caglion, L., Gasparrini, F., Misiti, D., and Palmieri, G., Tetrahedron, 1978, vol. 34, p. 135. https://doi.org/10.1016/0040-4020(78)88048-X
Hamann, H.-J. and Liebscher, J., J. Org. Chem., 2000, vol. 65, p. 1873. https://doi.org/10.1021/jo991457y
Hamann, H.-J., Bunge, A., and Liebscher, J., Chem. Eur. J., 2008, vol. 14, p. 6849. https://doi.org/10.1002/chem.200800932
Tsuchiya, K., Hamada, Y., Masuyama, A., Nojima, M., McCullough, K.J., Kim, H.-S., Shibata, Y., and Wataya, Y., Tetrahedron Lett., 1999, vol. 40, p. 4077. https://doi.org/10.1016/S0040-4039(99)00653-X
Robertson, J.C. and Verzino, W.J., J. Org. Chem., 1970, vol. 35, p. 545. https://doi.org/10.1021/jo00827a068
Razumovskii, S.D. and Zaikov, G.E., Ozon i ego reaktsii s organicheskimi soedineniyami (Ozon and Its Reactions with Organic Compounds), Moscow: Nauka, 1974.
Bailey, P.S., Ozonation in Organic Chemistry, New York: Academic Press, 1978, vol. 1, p. 25.
Emanuel’, N.M., Uspekhi khimii organicheskikh perekisnykh soedinenii i autookisleniya (Advances in the Chemistry of Organic Peroxy Compounds and Autooxidation), Moscow: Khimiya, 1969.
Adam, W., Four-Membered Ring Peroxides: 1,2-Dioxetanes and α-Peroxylactones, Patai, S., Ed., Chichester: Wiley, 1983, p. 829. https://doi.org/10.1002/9780470771730.ch24
Organic Peroxides, Ando, W., Ed., Chichester: Wiley, 1992.
Maltha, P.R.A. and Tijssen, S.B., US Patent no. 3409600A, 1968.
Matsuyama, K. and Kumura, H., J. Org. Chem., 1993, vol. 58, p. 1766. https://doi.org/10.1021/jo00059a029
Yasushi, S., Yasumasa, W., Hiromi, K., Tomoyuki, N., Shuji, S., and Yasuhiko, S., Bull. Chem. Soc. Jpn., 1992, vol. 65, p. 664. https://doi.org/10.1246/bcsj.65.664
Nwoko, D., Wells, M.O., and Bock, L.A., WO Patent Appl. Pub. no. 2003000655, 2003.
Rieche, A., Bischoff, C., and Dietrich, P., Chem. Ber., 1961, vol. 94, p. 2932. https://doi.org/10.1002/cber.19610941115
Nazarova, Z.F., Bocharova, Y.E., Batog, A.E., and Romantsevich, M.K., J. Org. Chem. USSR, 1966, vol. 2, p. 249.
Augusto, P., Giuliano, B., Carlo, B., Augusto, P.C., and Spartaco, F., US Patent no. 3296184A, 1967.
Yurzhenko, T.I., Elagin, G.I., Karpenko, A.N., and Mamchur, L.P., Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1970, vol. 13, p. 1457.
Schweitzer-Chaput, B., Boess, E., and Klussmann, M., Org. Lett., 2016, vol. 18, p. 4944. https://doi.org/10.1021/acs.orglett.6b02419
Oldekop, Y.A., Moiseichuk, K.L., Yuvchenko, A.P., and Isahanyan, A.L., Vestsi Akad. Navuk BSSR, Ser. Khim. Navuk, 1976, no. 2, p. 105.
Bloodworth, A.J. and Bunce, R.J., J. Organomet. Chem., 1973, vol. 60, p. 11. https://doi.org/10.1016/S0022-328X(00)85432-7
Chapurkin, V.V. and Drevin, V.E., Russ. J. Org. Chem., 1999, vol. 35, p. 1551.
Sorokina, A.N., Batog, A.E., and Romantsevich, M.K., J. Org. Chem. USSR, 1967, vol. 3, p. 827.
Mashnenko, O.M., Sorokina, A.N., Batog, A.E., Mironenko, N.I., and Romancevich, M.K., Sov. Prog. Chem. (Engl. Transl.), 1971, vol. 37, p. 97.
Schulz, M. and Likowski, K., Z. Chem., 1980, vol. 20, p. 53. https://doi.org/10.1002/zfch.19800200205
Wang, X., Pan, Y., Huang, K.-W., and Lai, Z., Org. Lett., 2015, vol. 17, p. 5630. https://doi.org/10.1021/acs.orglett.5b02881
Yuvchenko, A.P., Beresnevich, L.B., Zhukovskaya, N.A., Kozlov, N.G., Moiseichuk, K.L., and Oldekop, Y.A., J. Org. Chem. USSR, 1988, vol. 24, p. 1703.
Terent’ev, A.O., Kutkin, A.V., Troizky, N.A., Ogibin, Y.N., and Nikishin, G.I., Synthesis, 2005, vol. 2005, p. 2215. https://doi.org/10.1055/s-2005-872093
Schweitzer-Chaput, B., Sud, A., Pintér, Á., Dehn, S., Schulze, P., and Klussmann, M., Angew. Chem., Int. Ed., 2013, vol. 52, p. 13228. https://doi.org/10.1002/anie.201306752
Matsuyama, K., Sugiura, T., and Minoshima, Y., J. Org. Chem., 1995, vol. 60, p. 5520. https://doi.org/10.1021/jo00122a035
Mukaiyama, T., Miyoshi, N., Kato, J.-I., and Ohshima, M., Chem. Lett., 1986, vol. 15, p. 1385. https://doi.org/10.1246/cl.1986.1385
Buncel, E. and Davies, A.G., J. Chem. Soc., 1958, p. 1550. https://doi.org/10.1039/JR9580001550
Dauben, J.H., Honnen, L., and Harmon, K., J. Org. Chem., 1960, vol. 25, p. 1442. https://doi.org/10.1021/jo01078a608
Hamada, Y., Tokuhara, H., Masuyama, A., Nojima, M., Kim, H.-S., Ono, K., Ogura, N., and Wataya, Y., J. Med. Chem., 2002, vol. 45, p. 1374. https://doi.org/10.1021/jm010473w
McCullough, K.J., Ito, T., Tokuyasu, T., Masuyama, A., and Nojima, M., Tetrahedron Lett., 2001, vol. 42, p. 5529. https://doi.org/10.1016/S0040-4039(01)01015-2
Kyasa, S., Puffer, B.W., and Dussault, P.H., J. Org. Chem., 2013, vol. 78, p. 3452. https://doi.org/10.1021/jo4001564
Ito, T., Tokuyasu, T., Masuyama, A., Nojima, M., and McCullough, K.J., Tetrahedron, 2003, vol. 59, p. 525. https://doi.org/10.1016/S0040-4020(02)01556-9
Ghorai, P. and Dussault, P.H., Org. Lett., 2009, vol. 11, p. 4572. https://doi.org/10.1021/ol9018216
Dussault, P.H., Lee, I.Q., Lee, H.-J., Lee, R.J., Niu, Q.J., Schultz, J.A., and Zope, U.R., J. Org. Chem., 2000, vol. 65, p. 8407. https://doi.org/10.1021/jo991714z
Milas, N.A. and Klein, R.J., J. Org. Chem., 1968, vol. 33, p. 848. https://doi.org/10.1021/jo01266a084
Kropf, H., Bernert, C.R., and Dahlenburg, L., Tetrahedron, 1970, vol. 26, p. 3279. https://doi.org/10.1016/S0040-4020(01)92907-2
Cardinale, G., Laan, J.A.M., and Ward, J.P., Tetrahedron, 1985, vol. 41, p. 2899. https://doi.org/10.1016/S0040-4020(01)96613-X
Cooper, W. and Davison, W.H.T., J. Chem. Soc., 1952, p. 1180. https://doi.org/10.1039/JR9520001178
Kerur, D.R. and Diaper, D.G.M., Can. J. Chem., 1973, vol. 51, p. 3110. https://doi.org/10.1139/v73-463
Zang, N., Qian, X.-M., Liu, Z.-Y., and Shu, C.-M., J. Therm. Anal. Calorim., 2016, vol. 124, p. 1131. https://doi.org/10.1007/s10973-015-5209-5
Lee, B., Story, P.R., and Sanderson, J.R., J. Org. Chem., 1976, vol. 41, p. 2314. https://doi.org/10.1021/jo00875a021
Tyumkina, T.V., Makhmudiyarova, N.N., Kiyamutdinova, G.M., Meshcheryakova, E.S., Bikmukhametov, K.S., Abdullin, M.F., Khalilov, L.M., Ibragimov, A.G., and Dzhemilev, U.M., Tetrahedron, 2018, vol. 74, p. 1749. https://doi.org/10.1016/j.tet.2018.01.045
Terent’ev, A.O., Platonov, M.M., Krylov, I.B., Chernyshev, V.V., and Nikishin, G.I., Org. Biomol. Chem., 2008, vol. 6, p. 4435. https://doi.org/10.1039/B809661A
Criegee, R. and Metz, K., Chem. Ber., 1956, vol. 89, p. 1714. https://doi.org/10.1002/cber.19560890720
Bunge, A., Hamann, H.-J., Dietz, D., and Liebscher, J., Tetrahedron, 2013, vol. 69, p. 2446. https://doi.org/10.1016/j.tet.2013.01.032
Bunge, A., Hamann, H.-J., McCalmont, E., and Liebscher, J., Tetrahedron Lett., 2009, vol. 50, p. 4629. https://doi.org/10.1016/j.tetlet.2009.05.096
Milas, N.A. and Golubović, A., J. Am. Chem. Soc., 1959, vol. 81, p. 3361. https://doi.org/10.1021/ja01522a051
Sanderson, J.R. and Zeiler, A.G., Synthesis, 1975, vol. 1975, p. 388. https://doi.org/10.1055/s-1975-23765
Busch, P. and Story, P.R., Synthesis, 1970, vol. 1970, p. 181. https://doi.org/10.1055/s-1970-21592
Terent’ev, A.O., Platonov, M.M., Sonneveld, E.J., Peschar, R., Chernyshev, V.V., Starikova, Z.A., and Nikishin, G.I., J. Org. Chem., 2007, vol. 72, p. 7237. https://doi.org/10.1021/jo071072c
Hawkins, E.G.E., J. Chem. Soc. C, 1969, p. 2671. https://doi.org/10.1039/J39690002671
Franco, L.L., de Almeida, M.V., e Silva, L.F.R., Vieira, P.P.R., Pohlit, A.M., and Valle, M.S., Chem. Biol. Drug Des., 2012, vol. 79, p. 790. https://doi.org/10.1111/j.1747-0285.2012.01345.x
McCapra, F. and Leeson, P., J. Chem. Soc., Chem. Commun., 1976, p. 1037. https://doi.org/10.1039/C39760001037
Paul, K., Story, P.R., Busch, P., and Sanderson, J.R., J. Org. Chem., 1976, vol. 41, p. 1283. https://doi.org/10.1021/jo00869a054
Terent’ev, A.O., Kutkin, A.V., Platonov, M.M., Starikova, Z.A., Ogibin, Y.N. and Nikishina, G.I., Russ. Chem. Bull., Int. Ed., 2005, vol. 54, p. 1214. https://doi.org/10.1007/s11172-005-0383-4
Arzumanyan, A.V., Terent’ev, A.O., Novikov, R.A., Lakhtin, V.G., Chernyshev, V.V., Fitch, A.N., and Nikishin, G.I., Eur. J. Org. Chem., 2014, vol. 2014, p. 6877. https://doi.org/10.1002/ejoc.201402895
Belič, I., Kastelic-Suhadolc, T., Kavčič, R., Marsel, J., Kramer, V., and Kralj, B., Tetrahedron, 1976, vol. 32, p. 3045. https://doi.org/10.1016/0040-4020(76)80164-0
Clover, A.M., J. Am. Chem. Soc., 1924, vol. 46, p. 419. https://doi.org/10.1021/ja01667a017
Milas, N.A., Chem. Rev., 1932, vol. 10, p. 295. https://doi.org/10.1021/cr60036a002
Funding
This study was performed under financial support by the Russian Science Foundation (project no. 21-43-04417).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
The authors declare no conflict of interest.
Additional information
Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 6, pp. 757–787 https://doi.org/10.31857/S051474922106001X.
Rights and permissions
About this article
Cite this article
Bityukov, O.V., Vil’, V.A. & Terent’ev, A.O. Synthesis of Acyclic Geminal Bis-peroxides. Russ J Org Chem 57, 853–878 (2021). https://doi.org/10.1134/S1070428021060014
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428021060014