dc.contributor.author	McCaw, Patrick G.
dc.contributor.author	Khandavilli, Udaya Bhaskara Rao
dc.contributor.author	Lawrence, Simon E.
dc.contributor.author	Maguire, Anita R.
dc.contributor.author	Collins, Stuart G.
dc.contributor.funder	Science Foundation Ireland	en
dc.contributor.funder	Irish Research Council	en
dc.date.accessioned	2019-02-14T11:22:40Z
dc.date.available	2019-02-14T11:22:40Z
dc.date.issued	2018-12-12
dc.date.updated	2019-02-14T10:20:26Z
dc.description.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.	en
dc.description.sponsorship	Science Foundation Ireland (05/PICA/B802/EC07)	en
dc.description.status	Peer reviewed	en
dc.description.version	Accepted Version	en
dc.format.mimetype	application/pdf	en
dc.identifier.citation	McCaw, P. G., Khandavilli, U. B. R., Lawrence, S. E., Maguire, A. R. and Collins, S. G. (2018) 'Synthesis of 1,2,5-oxathiazole-S-oxides by 1,3 dipolar cycloadditions of nitrile oxides to α-oxo sulfines', Organic and Biomolecular Chemistry, 17(3), pp. 622-638. doi:10.1039/C8OB02691B	en
dc.identifier.doi	10.1039/C8OB02691B
dc.identifier.endpage	638	en
dc.identifier.issn	1477-0520
dc.identifier.issn	1477-0539
dc.identifier.issued	3	en
dc.identifier.journaltitle	Organic and Biomolecular Chemistry	en
dc.identifier.startpage	622	en
dc.identifier.uri	https://hdl.handle.net/10468/7494
dc.identifier.volume	17	en
dc.language.iso	en	en
dc.publisher	Royal Society of Chemistry	en
dc.relation.project	info:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/	en
dc.rights	© 2018, the Authors. Published by the Royal Society of Chemistry. All rights reserved.	en
dc.subject	Rhodium acetate	en
dc.subject	Catalyst	en
dc.subject	Kinetic isomers	en
dc.subject	Continuous flow thermolysis	en
dc.subject	Thermodynamic isomers	en
dc.title	Synthesis of 1,2,5-oxathiazole-S-oxides by 1,3 dipolar cycloadditions of nitrile oxides to α-oxo sulfines	en
dc.type	Article (peer-reviewed)	en

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

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