C.S. Angadiyavar, J. Cornelisse, et al.
Tetrahedron Letters
Pyrolysis of tetracyclo[5.3.0.02,10.03,6]decene-8 (V) (believed to be 3,6-endo) in the vapor phase (~100 Torr) in a static system at 250° gave three isomeric products in the ratio of 4:2:1. The first of these was tricyclo-[5.2.1.04,10]deca-2,5-diene (VI). The second was found to be the exo stereoisomer (VIII) of the starting material. The third isomer was not further identified. In a fast-flow system at 550° at a pressure of <1 Torr, the products were VI and 1,2-dihydronaphthalene. From kinetic studies and by deuterium labeling, the formation of VI was shown to involve a shift of the C3C4 bond in V to the C8 position. Thus, this reaction can be regarded as the rearrangement of a (2′-vinylcyclopropyl)cyclobutane system to a 1,4-cyclononadiene. © 1970, American Chemical Society. All rights reserved.
C.S. Angadiyavar, J. Cornelisse, et al.
Tetrahedron Letters
Ivan Haller, R. Srinivasan
JACS
R. Srinivasan, Sheldon E. Cremer
Journal of Physical Chemistry
R. Srinivasan
International Journal of Chemical Kinetics