Die sterischen Bedingungen der Fragmentierungsreaktion I. Teil. Stereoisomere 3‐Chlortropane. Fragmentierungsreaktionen, 14. Mitteilung

Abstract

Abstract The steric requirements for the synchronous fragmentation of γ‐aminohalides as previously postulated have been confirmed by a study of the solvolysis of stereoisomeric 3β‐ and 3β‐chloro‐tropanes and ‐nortropanes. 3β‐chloro‐tropanes ( 7 a ) and 3β‐chloro‐nortropane ( 7 b ), which fulfil the stereoelectronic requirements, undergo quantitative fragmentation in 80 vol.% ethanol. They react 1.35 × 10 4 and 1.35 × 10 3 times, respectively, as fast as the ‘homomorphous’ exo ‐3‐chloro‐bicyclo[3.2.1]octane ( 12 a ). Fragmentation therefore takes place by the synchronous mechanism.