Use of trans-1-vinyl-6-acetoxy- and t rans-1-vinyl-6-ethylenedioxy-9-methyl-?1octalins in diene synthesis reactions

Transformations of cyclopropanol intermediates. 3. Ring-opening reactions of 6-methyl-5-hydroxytricyclo[4.4.0.01,5]decan-9-one

“…In contrast, the base-catalyzed isomerization of 19 is poorly regioselective and proceeds with opposite stereoselectivity in the formation of the two products 20 and 21 (the former is generated with retention of configuration and the latter with inversion). Since a molecular model (Dreiding) of 19 does not disclose any obvious steric hindrance associated with the bridging chain, we believe that these results may reflect rather subtle distortions of the bicyclo[4.1.0]heptane skeleton induced by the three-carbon bridge.…”

“…The latter component was confirmed by a mixture melting point with authentic 3 (mp 65 °C). 21 Reaction of 1 with Aqueous Ferric Chloride. A 1-g sample of cyclopropanol 1 (5.5 mmol) was added in one portion to a stirred solution of ferric chloride (4 g) in 25 mL of water.…”