Dissecting a dyotropic rearrangement

The Journal of Organic Chemistry
Rebecca L Davis, Dean J Tantillo

Abstract

Herein we describe density functional theory calculations on nitroso acetal-to-aminal rearrangements reported by Denmark and co-workers. Our calculations indicate that various structural (ring strain, hyperconjugation, anomeric effects) and environmental (both specific and nonspecific solvation) factors greatly influence the ease of rearrangement. Our calculations also indicate that both concerted and stepwise mechanisms are energetically viable.

References

Nov 26, 2002·The Journal of Organic Chemistry·Martin EipertMartin E Maier
Apr 24, 2003·Journal of the American Chemical Society·Xiyun ZhangSamuel J Danishefsky
Aug 31, 2006·Journal of the American Chemical Society·Scott E DenmarkLaurenz A Kramps
Oct 19, 2007·The Journal of Organic Chemistry·Young J Hong, Dean J Tantillo
Sep 15, 2009·Chemical Reviews·Israel FernándezMiguel A Sierra

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Citations

Feb 10, 2017·Natural Product Reports·Cedric L Hugelshofer, Thomas Magauer
Jun 24, 2017·Organic Letters·Hugo SantallaCarlos Silva López
Nov 28, 2013·Angewandte Chemie·Aicha BoudharJean Suffert
Dec 12, 2013·Organic & Biomolecular Chemistry·Michael W LodewykDean J Tantillo

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