Investigations of the Thermal Responsiveness of 1, 4, 2‐Oxathiazoles. Issue 30 (14th September 2015)

• Record Type: Journal Article
• Authors: Hewitt, Russell J.; Ong, Michelle Jui Hsien; Lim, Yi Wee; Burkett, Brendan A.
• Is Part Of: European journal of organic chemistry. Issue 30(2015)
• Page Start: 6687
• Page End: 6700
• Publication Date: 2015-09-14
• Subjects: Nitrogen heterocycles -- Sulfur heterocycles -- Oxygen heterocycles -- Rearrangement -- Substituent effects -- Fragmentation -- Structure–activity relationships; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500909
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The first systematic study of the thermal rearrangement/fragmentation of 5, 5‐disubstituted 1, 4, 2‐oxathiazoles into isothiocyanates is reported. Structure–activity relationships reveal that the choice of substituent at the 5‐position of the 1, 4, 2‐oxathiazoles is the predominant factor to influence the ease of fragmentation. Abstract : The first systematic study of the thermal rearrangement/fragmentation of 5, 5‐disubstituted 1, 4, 2‐oxathiazoles into isothiocyanates is reported. Structure–activity relationships reveal that the choice of substituent at the 5‐position of the 1, 4, 2‐oxathiazoles not only influences the ease of fragmentation but may also have mechanistic consequences on the reaction.