Synthesis, bromination, and photoelectron spectra of meso-bridgehead dienes

KJ Shea, AC Greeley, S Nguyen…

Index: Shea,K.J.; Greeley,A.L.; Nguyen,S. Journal of the American Chemical Society, 1986 , vol. 108, p. 5901

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Citation Number: 23

Abstract

Abstract: The Cope rearrangement of l, n-divinylbicycloalkanes has been employed for the synthesis of a series of meso-bridgehead dienes, molecules that contain two torsionally distorted carbon-carbon double bonds held in proximate relationship. The rate of Cope rearrangement does not correlate with reaction exothermicity or release of strain energy. A frontier molecular orbital explanation is one of several considerations offered to account ...