High Reactivity of Strained Seven-Membered-Ring trans-Alkenes

Jillian R. Sanzone, K. A. Woerpel

Research output: Contribution to journalArticle

Abstract

trans-Oxasilacycloheptenes are highly reactive strained alkenes. Competition reactions showed that these seven-membered ring trans-alkenes underwent [4+2] cycloaddition reactions faster than a trans-cyclooctene. They also reacted with quinones and dimethyl acetylenedicarboxylate to form adducts with high diastereoselectivity. Kinetic studies showed that ring strain increases nucleophilicity by approximately 109. trans-Oxasilacycloheptenes are strained seven-membered-ring trans-alkenes that underwent [4+2] cycloaddition reactions faster than a bicyclic trans-cyclooctene. They also reacted with quinones and dimethyl acetylenedicarboxylate to form adducts with high diastereoselectivity. Kinetic studies showed that ring strain increases nucleophilicity by approximately 109.

Original languageEnglish (US)
Pages (from-to)790-793
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number2
DOIs
StatePublished - Jan 11 2016

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Keywords

  • alkenes
  • cycloaddition
  • cycloheptenes
  • silicon
  • strained molecules

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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