The stereochemistry of solvolysis for 2-adamantyl derivatives, and the non-classical carbonium ion question

Abstract

When derivatives of adamantan-2-ol solvolyse they usually exhibit a preference for retention of configuration; as they also rearrange skeletally to some extent, the 2-adamantyl cation meets, in some measure, two of the familiar criteria for delocalisation of C–C σ-electrons, hence general conclusions regarding “non-classical carbonium ions” are drawn.