S. Cremer, R. Srinivasan
JACS
Thermal isomerization of cis-4,5-dimethyl-endo-tetracyclo[5.3.0.02,10.03,6]decene-8 (IX) at 300° gave rise to endo, cis-8,9-dimethyltricyclo[2.2.1.04,10]deca-2,5-diene (XII) as the major isomeric product. The reaction, which is a typical (2′-vinylcyclopropyl)cyclobutane rearrangement, thus proceeds with retention of the stereochemistry at the migrating σ bond. Arguments are presented to show that this rearrangement is distinct from the homo [1,5] sigmatropic shift which in the tricyclo[3.3.0.02,8]octene-3 systems involves the migration of hydrogen atoms only. It is also distinct from, although related to, the vinylcyclopropane rearrangement. The use of the (2′-vinylcyclopropyl)cyclobutane rearrangement in synthesis is exemplified by the preparation of endo-tetracyclo[8.2.1.02,6.-077,13]trideca-3,8,11-triene (VII) from benzene and 1,3,5-cycloheptatriene in three steps. © 1972, American Chemical Society. All rights reserved.
S. Cremer, R. Srinivasan
JACS
R. Srinivasan, John C. Powers Jr.
The Journal of Chemical Physics
R. Srinivasan, F.I. Sonntag
Tetrahedron Letters
R. Srinivasan
JACS