Rearrangements of pinane derivatives. Part VI. Rearrangement via a [1,3] shift of carbon during reaction of 2αH-10-aminopinane (cis-myrtanylamine) with nitrous acid

Abstract

Reaction of 2αH-10-aminopinane (cis-mytranylamine) with nitrous acid gives a product mixture which includes six different rearranged carbon skeletons. In addition to rearrangement observed in the ester solvolysis, ring expansion to the bicyclo[4.1.1]octane system is observed, together with an unusual ring expansion via a [1,3] carbon shift to give the bicyclo[2.2.2]octane system.