B. Halton, S. G. G. Russell
1992
Citations
0
Influential Citations
2
Citations
Journal
Australian Journal of Chemistry
Abstract
The dichloromethylene -bridged annulene (5) is available in four steps (47%) from 1,4,5,8-tetrahydronaphthalene (11) via the dibromide (15); the minor (5%) product of dehydrobromination of (15) is 2-bromo-9,9-dichloro-1,4-dihydro-4a,8a-methanonaphthalene (16). Dichlorocarbene adds to the norcaradiene form of (5) to give adduct (6) with 80% efficiency. Diene (6) resists both [π4+π2] cycloadditions and reductive dechlorination. Neither (5) nor parent 1,6-methano[10] annulene (18) adds methylene from Simmons-Smith cyclopropanation procedures.