The Journal of Organic Chemistry

Thermal isomerization of a vinylcyclobutene to a cyclohexadiene

GC Paul, JJ Gajewski

Index: Paul, Gitendra C.; Gajewski, Joseph J. Journal of Organic Chemistry, 1992 , vol. 57, # 7 p. 1970 - 1973

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Citation Number: 6

Abstract

Above 100 OC 5methyleneapiro [3.5] non-l-ene, 1, undergcea cyclobutene ring opening to Q-triene 2 and apparent 1, 3-shift to a hexahydronaphthalene, 3, in a 3 to 1 ratio.@)-Triene 2 gives 3 in a competitive reaction. The activation energies for all three processes are obtained from a kinetic simulation at three temperatures. It is likely that the (Z)-triene 4, also derived by cyclobutene ring opening, is an intermediate in the 1 to 3 conversion. ...