Transposition bis-homoallénylique: solvolyse de γ-tosylates alléniques

Cyclisation (formation of derivatives of 2-methylidene-cyclopentanol or cyclohexanone) with inversion of configuration and retention of optical activity is observed during the solvolysis of secondary γ-allenic tosylates. Steric factors rather than electronic ones control the participation of one of the double bonds in the allenic system. Kinetic results and product distribution are discussed.