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Die Solvolyse von exo ‐ und endo ‐3‐Chlor‐bicyclo[3.2.1]octan
Author(s) -
Grob C. A.,
Weiss A.
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.19660490826
Subject(s) - chemistry , solvolysis , epimer , bicyclic molecule , octane , steric effects , medicinal chemistry , chloride , stereochemistry , organic chemistry , hydrolysis
The rates of solvolysis of exo and endo 3‐chloro bicyclo[3.2.1]octane 1a and 2a have been measured in 80 vol.% aqueous ethanol. The axial endo chloride reacts 263 times as fast as the equatorial exo epimer. This remarkably large rate difference is ascribed to sterically accelerated ionisation of the axial endo epimer due to the ethano bridge.