ISSN:
0947-3440
Keywords:
Cope rearrangements
;
PE spectroscopy
;
Paterno-Büchi reactions
;
Tricyclo[4.3.0.03,8]nonanes
;
Through-bond and through-space interactions
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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-Büchi 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.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199519950245
Permalink