High Reactivity of Strained Seven-Membered-Ring trans-Alkenes
Jillian R. Sanzone
Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003 (USA)
Search for more papers by this authorCorresponding Author
Prof. K. A. Woerpel
Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003 (USA)
Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003 (USA)Search for more papers by this authorJillian R. Sanzone
Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003 (USA)
Search for more papers by this authorCorresponding Author
Prof. K. A. Woerpel
Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003 (USA)
Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003 (USA)Search for more papers by this authorGraphical Abstract
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.
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.
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