Die sterischen Bedingungen der Fragmentierungsreaktion I. Teil. Stereoisomere 3-Chlortropane. Fragmentierungsreaktionen, 14. Mitteilung |
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Authors: | A T Bottini C A Grob E Schumacher J Zergenyi |
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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 × 104 and 1.35 × 103 times, respectively, as fast as the ‘homomorphous’ exo-3-chloro-bicyclo3.2.1]octane ( 12 a ). Fragmentation therefore takes place by the synchronous mechanism. |
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