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Sulfur–Nitrogen and Carbon–Nitrogen Bond Formation by Intermolecular Imination and Amidation without Catalyst
Author(s) -
Ma Wen Bo,
Li Sheng Nan,
Zhou Zhong Hua,
Shen Heng Shui,
Li Xue,
Sun Qiu,
He Ling,
Xue Ying
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101463
Subject(s) - chemistry , nitrene , nitrogen , catalysis , reactivity (psychology) , sulfur , amine gas treating , intermolecular force , bond dissociation energy , organic chemistry , dissociation (chemistry) , polymer chemistry , photochemistry , molecule , medicine , alternative medicine , pathology
Imination and amidation of sulfides, sulfoxides, and olefins using 4 H ‐1,2,4‐triazole‐4‐amine as a nitrogen source with PhI(OAc) 2 as an oxidant were achieved in moderate to high yields without the addition of a catalyst. The carbon–nitrogen and sulfur–nitrogen bond forming reactivity is consistent with a nitrene insertion mechanism in which the reactivity generally increases with decreasing N–H bond dissociation energy of the nitrogen source and increasing oxidation potential of the oxidant.