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Conjugate acid structure for oxaziridines bearing primary and secondary 2‐alky 1 groups
Author(s) -
Challis Brian C.,
Lobo Ana M.
Publication year - 1977
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570140820
Subject(s) - chemistry , protonation , conjugate , carbon atom , chloroform , conjugate acid , hydrolysis , primary (astronomy) , medicinal chemistry , atom (system on chip) , carbon tetrachloride , stereochemistry , organic chemistry , ring (chemistry) , ion , mathematical analysis , physics , mathematics , astronomy , computer science , embedded system
The protonation of five representative oxaziridines is reported for inert solvents (deuterio‐chloroform or carbon tetrachloride) where conjugate acid formation may be effected by the addition of about 20% (v/v) TFA. Comparison of the 1 H nmr chemical shifts for neutral and conjugate acid forms suggests that oxaziridines usually undergo protonation on the N ‐atom under these conditions. For one compound studied, 2‐ethyl‐3‐ p ‐nitrophenyloxaziridine, there is a possibility that protonation occurs on the alternative O ‐atom. The relevance of these findings to the mechanism of the acid‐catalysed hydrolysis of oxaziridines is discussed.