High Reactivity of Strained Seven‐Membered‐Ring  trans ‐Alkenes | Zendy

Sanzone Jillian R. | Zendy; Woerpel K. A. | Zendy

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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 .

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