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

Full Text: HTML

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. ...

Photochemistry of cyclopentenones: tricyclo [4.3. 2.0] undecenones and tricyclo [3.3. 3.0] undecenones

[Cargill, Robert L.; Peet, Norton P.; Pond, David M.; Bundy, William A.; Sears, A. Bradford Journal of Organic Chemistry, 1980 , vol. 45, # 20 p. 3999 - 4001]

Silver (I) catalyzed rearrangements of strained. sigma. bonds. 38. Regiospecificity of cyclopropylidene carbon-hydrogen insertion reactions within [mn 1] propellane …

[Paquette,L.A.; Chamot,E.; Brown,A.R. Journal of the American Chemical Society, 1980 , vol. 102, p. 637]

(2-vinylcyclopropyl) carbenes. More stepwise mechanisms for ring-expansion

[Cummins, Jordan M.; Pelczer, Istvan; Jones Jr., Maitland Journal of the American Chemical Society, 1999 , vol. 121, # 33 p. 7595 - 7599]