title: High Reactivity of Strained Seven-Membered-Ring trans-Alkenes.
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 10(9).
authors.affiliation: Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003 (USA).
authors.forename: Jillian R
authors.initials: JR
authors.lastname: Sanzone
authors.affiliation: Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003 (USA). kwoerpel@nyu.edu.
authors.forename: K A
authors.initials: KA
authors.lastname: Woerpel
keywords: alkenes; cycloaddition; cycloheptenes; silicon; strained molecules