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Die sterischen Bedingungen der Fragmentierungsreaktion I. Teil. Stereoisomere 3‐Chlortropane. Fragmentierungsreaktionen, 14. Mitteilung
Author(s) -
Bottini A. T.,
Grob C. A.,
Schumacher E.,
Zergenyi J.
Publication year - 1966
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19660490815
Subject(s) - chemistry , solvolysis , steric effects , fragmentation (computing) , octane , bicyclic molecule , stereochemistry , medicinal chemistry , organic chemistry , hydrolysis , computer science , operating system
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.