The Dual Reactivity of 5-S/5-O-Phenyl-1,4,2-oxathiazoles: A Fragmentation Pathway That Affords Nitriles in the Presence of Water

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. An unpreceden...

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Bibliographic Details
Published in:European journal of organic chemistry 2015-08, Vol.2015 (22), p.4840-4842
Main Authors: Lim, Yi Wee, Hewitt, Russell J., Burkett, Brendan A.
Format: Article
Language:English
Subjects:
1,4,2‐Oxathiazole
2-Oxathiazole
Fragmentation
Nitriles
Reaction mechanisms
Rearrangement
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Summary: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. An unprecedented rearrangement of 5‐phenyl‐1,4,2‐oxathiazoles bearing a C5 leaving group to nitriles in the presence of water is described.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500637