A pseudopericyclic [3,5]-sigmatropic rearrangement of a coumarin trichloroacetimidate derivative

Trideep Rajale, Shikha Sharma, Daniel K. Unruh, Daniel A. Stroud, David M. Birney

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

Thermolysis of a coumarin trichloroacetimidate yields a single rearrangement product. The proposed mechanism is a pseudopericyclic allowed (Woodward-Hoffman forbidden) [3,5]-sigmatropic rearrangement to form the corresponding amide followed by a sigmatropic [1,5]-hydrogen migration. Transition state calculations at the B3LYP/6-31G(d,p) level support this mechanism and suggest the selectivity is influenced by the stability of the intermediates.

Original languageEnglish
Pages (from-to)874-879
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number6
DOIs
StatePublished - 2018

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