Reactivity of Geometrically Constrained Cyclopropylcarbinyl and Homoallyl Substrates. Solvolysis of 2,4-Dehydro-5-homoadamantyl and 2-Homoadamant-4-enyl Derivatives

Article abstract of DOI:10.1021/jo00135a010

Solvolysis of 5-endo-2,4-dehydrohomoadamantyl 3,5-dinitrobenzoate (5) or 2-exo-chloro-4-homoadamantene (6) in buffered 70percent aqueous acetone gives a very similar mixture of products by way of an apparent common intermediate.The formation of 5-endo-hyd