Issue 3, 2019

Synthesis of 1,2,5-oxathiazole-S-oxides by 1,3-dipolar cycloadditions of nitrile oxides to α-oxo sulfines

Abstract

Synthetic methodology for the generation of novel 1,2,5-oxathiazole-S-oxides from cycloaddition of nitrile oxide dipoles with α-oxo sulfines generated in situ via the α-sulfinyl carbenes derived from α-diazosulfoxides is described. Experimental evidence and mechanistic rationale for the unanticipated interconversion of the diastereomeric 1,2,5-oxathiazole-S-oxide cycloadducts are discussed. Notably, using rhodium acetate as a catalyst at 0 °C under traditional batch conditions led to the selective formation and isolation of the kinetic isomers, while, in contrast, using continuous flow thermolysis, optimal conditions for the synthesis and isolation of the thermodynamic isomers were established.

Graphical abstract: Synthesis of 1,2,5-oxathiazole-S-oxides by 1,3-dipolar cycloadditions of nitrile oxides to α-oxo sulfines

Supplementary files

Article information

Article type
Paper
Submitted
30 Okt 2018
Accepted
12 Dez 2018
First published
12 Dez 2018

Org. Biomol. Chem., 2019,17, 622-638

Synthesis of 1,2,5-oxathiazole-S-oxides by 1,3-dipolar cycloadditions of nitrile oxides to α-oxo sulfines

P. G. McCaw, U. B. R. Khandavilli, S. E. Lawrence, A. R. Maguire and S. G. Collins, Org. Biomol. Chem., 2019, 17, 622 DOI: 10.1039/C8OB02691B

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