Formation of unexpected products in the attempted aziridination of styrene with trifluoromethanesulfonyl nitrene
Formation of unexpected products in the attempted aziridination of styrene with trifluoromethanesulfonyl nitrene
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DOI：
10.1016/j.tet.2010.08.070
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发表时间：
2010-10-23
期刊：
影响因子：
2.1
通讯作者：
Schilde, Uwe
中科院分区：
文献类型：
--
作者：
Shainyan, Bagrat A.;Moskalik, Mikhail Yu.;Schilde, Uwe
苯乙烯与三氟甲磺酰胺生成的三氟甲磺酰基氮烯在t-BuOCl+NaI体系中反应，生成三氟-N-[2-苯基-2-（三氟甲磺酰基）氨乙基]甲磺酰胺、1-苯基-2-碘乙醇和2，5-二苯基-1，4-双（三氟甲磺酰基）哌嗪，而不是预期的氮杂环丙烷化产物2-苯基-1-（三氟甲磺酰基）氮杂环丙烷。对反应机理进行了讨论。(C)2010爱思唯尔有限公司版权所有。
The reaction of styrene with trifluoromethanesulfonyl nitrene generated from trifluoromethanesulfonamide in the system (t-BuOCl+NaI) results in the formation of trifluoro-N-[2-phenyl-2-(trifluoromethylsulfonyl) aminoethyl]methanesulfonamide, 1-pheny1-2-iodo-ethanol, and 2,5-diphenyl-1,4-bis(trifluoromethyl sulfonyl)piperazine rather than the expected product of aziridination, 2-phenyl-1-(trifluoromethylsulfonyl) aziridine. The mechanism of the reaction is discussed. (C) 2010 Elsevier Ltd. All rights reserved.