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S-Methyl diethylthiophosphinate in mono- and di(dechloromethylthioylation) of substituted benzylidene chlorides

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Abstract

The main route of a new reaction of (dichloromethyl)arenes with S-methyl diethylthiophosphinate is the attack of the thiol sulfur atom (P–SMe) on the methylene carbon atom. A new method for synthesizing dimethyl dithioacetals of arenecarbaldehydes without using highly toxic methanethiol was developed. The suggested approach involves di(dechloromethylthioylation) of the dichloromethyl group of (dichloromethyl)arenes with S-methyl diethylthiophosphinate at a reagent ratio of 1: 2.

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References

  1. M. B. Gazizov, T. N. Kachalova, R. F. Karimova, R. A. Hairullin, O. G. Sinyashin, Russ. J. Gen. Chem., 1997, 67, 1942.

    CAS  Google Scholar 

  2. M. B. Gazizov, T. N. Kachalova, R. F. Karimova, O. G. Sinyashin, Dokl. Chem., 1998, 359, 71.

    Google Scholar 

  3. V. V. Zverev, Ya. Ya. Villem, J. Struct. Chem., 1980, 21, 22.

    Article  Google Scholar 

  4. V. V. Zverev, Yu. P. Kitaev, Russ. Chem. Rev., 1977, 46, 791.

    Article  Google Scholar 

  5. B. C. Ranu, A. Saha, T. Mandal, Tetrahedron, 2009, 65, 2072; DOI: https://doi.org/10.1016/j.tet.2008.12.079.

    Article  CAS  Google Scholar 

  6. R. H. Cragg, J. P. N. Husband, Inorg. Nucl. Chem. Lett., 1970, 6, 773; DOI: https://doi.org/10.1016/0020-1650(70)80097-6.

    Article  CAS  Google Scholar 

  7. M. Pourshahbaz, M. Joshaghani, E. Rafiee, J. Shahmoradi, F. Emami, A. Iranpour, Tetrahedron Lett., 2009, 50, 5987; DOI: https://doi.org/10.1016/j.tetlet.2009.07.104.

    Article  CAS  Google Scholar 

  8. G. Drosten, P. Mischke, J. Voß, Chem. Ber., 1987, 120, 1757.

    Article  CAS  Google Scholar 

  9. G. Alonso, C. Alvarez-Ibarra, G. Orellana, M. L. Quiroga, Bull. Soc. Chim. Belg., 1989, 98, 215; DOI: https://doi.org/10.1002/bscb.19890980309.

    Article  CAS  Google Scholar 

  10. E. Campaigne, N. F. Chamberlain, B. E. Edwards, J. Org. Chem., 1962, 27, 135; DOI: https://doi.org/10.1021/jo01048a033.

    Article  CAS  Google Scholar 

  11. G. M. Kosolapoff, R. M. Watson, J. Am. Chem. Soc., 1951, 73, 5466.

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Kazan National Research Technological University, 68 ul. K. Marx, 420015, Kazan, Russian Federation

    M. B. Gazizov, G. D. Valieva, S. Yu. Ivanova, R. A. Khairullin, Yu. S. Kirillina, O. D. Khairullina & Sh. N. Ibragimov

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  1. M. B. Gazizov
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  2. G. D. Valieva
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  3. S. Yu. Ivanova
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  4. R. A. Khairullin
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  5. Yu. S. Kirillina
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  6. O. D. Khairullina
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  7. Sh. N. Ibragimov
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Correspondence to M. B. Gazizov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1889–1892, October, 2019.

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Gazizov, M.B., Valieva, G.D., Ivanova, S.Y. et al. S-Methyl diethylthiophosphinate in mono- and di(dechloromethylthioylation) of substituted benzylidene chlorides. Russ Chem Bull 68, 1889–1892 (2019). https://doi.org/10.1007/s11172-019-2642-9

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  • DOI: https://doi.org/10.1007/s11172-019-2642-9

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