STUDIES IN RING EXPANSION.
Final scientific rept. 1 Jan 63-31 Dec 66,
GLASGOW UNIV (SCOTLAND) DEPT OF CHEMISTRY
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New synthetic routes to seven-membered rings were developed from bicyclo 3,2,1 octane derivatives by reactions which sever the one carbon bridge. Cycloheptanones, cycloheptenes and a tropolone were obtained using this procedure. The cycloheptene synthesis was used to build the skeleton of the alkaloid colchicine and the tropolone synthesis provides a new and unambiguous route to beta-substituted tropolones. The conformation of a cycloheptene was shown to be the chair form. Attempts to construct large rings by a variant of this procedure were unsuccessful. Author
- Organic Chemistry