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High Reactivity of Strained Seven‐Membered‐Ring trans ‐Alkenes
Author(s) -
Sanzone Jillian R.,
Woerpel K. A.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201510056
Subject(s) - dimethyl acetylenedicarboxylate , cycloaddition , chemistry , reactivity (psychology) , ring strain , ring (chemistry) , nucleophile , cyclooctene , medicinal chemistry , adduct , stereochemistry , catalysis , organic chemistry , medicine , alternative medicine , pathology
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 .