The Dual Reactivity of 5‐S/5‐O‐Phenyl‐1, 4, 2‐oxathiazoles: A Fragmentation Pathway That Affords Nitriles in the Presence of Water. Issue 22 (2nd July 2015)

• Record Type: Journal Article
• Authors: Lim, Yi Wee; Hewitt, Russell J.; Burkett, Brendan A.
• Is Part Of: European journal of organic chemistry. Issue 22(2015)
• Page Start: 4840
• Page End: 4842
• Publication Date: 2015-07-02
• Subjects: Reaction mechanisms -- Fragmentation -- Rearrangement -- Nitriles -- 1, 4, 2‐Oxathiazole; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500637
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : An unprecedented rearrangement of 5‐phenyl‐1, 4, 2‐oxathiazoles bearing a C5 leaving group to nitriles in the presence of water is described.