R. Gleiter, T. Herb, O. Borzyk
Feb 1, 1995
Citations
0
Influential Citations
8
Citations
Journal
Liebigs Annalen
Abstract
The synthesis of 2,7,9-trimethylenetricyclo[4.3.0.03,8]nonane (8), 7,9-dimethylenetricyclo[4.3.0.03,8]nonan-2-one (15), and 2,9-dimethylenetricyclo[4.3.0.03,8]non-4-ene (9) has been achieved. The first key step of the synthesis is a Diels-Alder reaction. In the reaction sequence affording 8 and 15 the starting materials are 1,3-cyclohexadiene (10) and acetylallene (11) and in the synthesis of 9 the diene 16 and methyl vinylketone (17). Further key steps are an intramolecular Paterno-Buchi and an oxetane ring-opening reaction. Compound 8 as well as 15 rearrange to the corresponding triquinane derivatives according to a Cope rearrangement. The PE spectra of 8, 9, and 15 reveal a considerable through-space and through-bond interaction of the double bonds.