[3.3]Sigmatropic rearrangement of 1,n-divinyl bicyclo[n,m,o]alkanes results in formation of meso bridgeheaddienes that contain a ,-1,5-cycloalkadiene linkage
Synthesis, bromination, and photoelectron spectra of meso-bridgehead dienes
作者:K. J. Shea、A. C. Greeley、S. Nguyen、P. D. Beauchamp、D. H. Aue、J. S. Witzeman
DOI:10.1021/ja00279a040
日期:1986.9
The Cope rearrangement of l,n-divinylbicycloalkanes has been employed for the synthesis of a series of meso-bridgeheaddienes, 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