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Ring Opening of N ‐Sulfonyl Aziridines by Amines in Silica‐Water
Author(s) -
Li Tiantian,
Ma Xiaosi,
Qi Junmei,
Sun Feifei,
Ma Ning
Publication year - 2014
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201400300
Subject(s) - sulfonyl , chemistry , ring (chemistry) , primary (astronomy) , polymer chemistry , silica gel , organic chemistry , alkyl , physics , astronomy
Ring opening reactions of N ‐sulfonyl aziridines by primary and secondary amines in silica gel (SG)‐water system were achieved, which provided a mild, practical and environmentally benign method to synthesize mono‐ and bis‐sulfonyl substituted amines. When primary and secondary amines were used in excess, they reacted with N ‐sulfonyl aziridines smoothly at room temperature, mainly affording 1:1 ring opening products. Reactions of primary amines with 2 equiv. of aziridines produced 2:1 ring opening products. Some 1:1 products can be cyclized with CS 2 to synthesize N ‐sulfonyl cyclothioureas also in water.