Peer-Reviewed Journal Details
Mandatory Fields
McCaw, Patrick G., Khandavilli, U. B. Rao,Lawrence, Simon E.,Maguire, Anita R.,Collins, Stuart G.
2018
December
Organic & Biomolecular Chemistry
Synthesis of 1,2,5-oxathiazole-S-oxides by 1,3-dipolar cycloadditions of nitrile oxides to a-oxo sulfines
Validated
Optional Fields
17
3
622
638
Synthetic methodology for the generation of novel 1,2,5-oxathiazole-S-oxides from cycloaddition of nitrile oxide dipoles with a-oxo sulfines generated in situ via the a-sulfinyl carbenes derived from a-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. ER
1477-0520
http://dx.doi.org/10.1039/C8OB02691B
10.1039/C8OB02691B
Grant Details