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Chlorination of Conjugated Nitroalkenes with PhICl2 and SO2Cl2 for the Synthesis of α-Chloronitroalkenes
Synthesis ( IF 2.2 ) Pub Date : 2020-05-14 , DOI: 10.1055/s-0040-1707396 Andrey A. Tabolin 1 , Anastasia A. Fadeeva 1, 2 , Sema L. Ioffe 1
Synthesis ( IF 2.2 ) Pub Date : 2020-05-14 , DOI: 10.1055/s-0040-1707396 Andrey A. Tabolin 1 , Anastasia A. Fadeeva 1, 2 , Sema L. Ioffe 1
Affiliation
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Chlorination of conjugated nitroalkenes with iodobenzene dichloride or sulfuryl chloride to give target α-chloronitroalkenes in good yields is described. Details of the procedure depend on the donating ability of the nitroalkene substituents. The activity of the described chlorinating agents increases in order ‘PhICl2/Py’ < ‘SO2Cl2’ < ‘SO2Cl2/HCl’ with the former producing the best yields for highly donating substrates and the latter for non-activated groups. An autocatalytic role of hydrogen chloride and the chemoselectivity of chlorination were also demonstrated.
中文翻译：
用PhICl2和SO2Cl2氯化共轭硝基烯烃以合成α-氯硝基烯烃
描述了用二氯化碘苯或磺酰氯对共轭硝基烯烃进行氯化，以高收率得到目标α-氯硝基烯烃。程序的细节取决于硝基烯烃取代基的给体能力。所描述的氯化剂的活性以'PhICl 2 / Py'<'SO 2 Cl 2 '<'SO 2 Cl 2 / HCl'的顺序增加，前者对于高施主底物产生最好的收率，而对于未活化的底物则产生最好的收率。组。还证明了氯化氢的自催化作用和氯化的化学选择性。
更新日期：2020-05-14
中文翻译：
用PhICl2和SO2Cl2氯化共轭硝基烯烃以合成α-氯硝基烯烃
描述了用二氯化碘苯或磺酰氯对共轭硝基烯烃进行氯化，以高收率得到目标α-氯硝基烯烃。程序的细节取决于硝基烯烃取代基的给体能力。所描述的氯化剂的活性以'PhICl 2 / Py'<'SO 2 Cl 2 '<'SO 2 Cl 2 / HCl'的顺序增加，前者对于高施主底物产生最好的收率，而对于未活化的底物则产生最好的收率。组。还证明了氯化氢的自催化作用和氯化的化学选择性。
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