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

Bottini A. T. | Zendy; Grob C. A. | Zendy; Schumacher E. | Zendy; Zergenyi J. | Zendy

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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.

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