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Issue 3, 2019
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Synthesis of 1,2,5-oxathiazole-S-oxides by 1,3-dipolar cycloadditions of nitrile oxides to α-oxo sulfines

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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

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Publication details

The article was received on 30 Oct 2018, accepted on 12 Dec 2018 and first published on 12 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02691B
Citation: Org. Biomol. Chem., 2019,17, 622-638
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    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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