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The Dual Reactivity of 5‐ S /5‐ O ‐Phenyl‐1,4,2‐oxathiazoles: A Fragmentation Pathway That Affords Nitriles in the Presence of Water
Author(s) -
Lim Yi Wee,
Hewitt Russell J.,
Burkett Brendan A.
Publication year - 2015
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.201500637
Subject(s) - chemistry , fragmentation (computing) , reactivity (psychology) , medicinal chemistry , decomposition , photochemistry , stereochemistry , organic chemistry , pathology , computer science , operating system , medicine , alternative medicine
The rearrangement of substituted 1,4,2‐oxathiazoles to nitriles in the presence of water is described. Preliminary investigations suggest that the reaction pathway proceeds via a 1,4,2‐oxathiazolium intermediate, followed by trapping with water and subsequent decomposition to products.