W. Trahanovsky, K. Koeplinger
Aug 1, 1992
Citations
0
Influential Citations
16
Citations
Journal
Journal of Organic Chemistry
Abstract
3-Methylene-1,4-pentadiene (8) and 1,2,3-trimethylenecyclohexane (10) are prepared in moderate to high yields in good purity by the flash vacuum pyrolysis of 1,5-diacetoxy-3-(acetoxymethyl)pentane (12) and 1,2,3-tris- (acetoxymethyl)cyclohexane (17), respectively. Triene 8 dimerizes cleanly at a moderate rate in benzene at 95 o C to give only one major product, [4+2] dimer 1,4,4-trivinylcyclohexene (13).It is conclued that the dimerization proceeds by a two steps mechanism:rate-determinating attack at the middle methylene group to form a resonance-stabilized diradical intermediate followed by rapid closure of the diradical to [4+2] dimer