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Nucleophilic Addition to C,C‐Double Bonds. Part VIII . The standard enthalpies of formation of anti 9,10 ‐10 endo ‐hydroxytricyclo [4.2.1.1 2,5 ]deca‐3,7‐dien‐9‐one and 9‐Oxatetracyclo [5.4.0.0 3,10 .0 4,8 ]undec‐5‐en‐2‐one and kinetic data for the cyclization of the olefinic alcohol to the ether
Author(s) -
Smeaton Alan A.,
Steele William V.,
Ramos Tombo Gerardo M.,
Ganter Camille
Publication year - 1983
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.19830660810
Subject(s) - chemistry , steric effects , intramolecular force , medicinal chemistry , double bond , nucleophilic addition , base (topology) , stereochemistry , nucleophile , ether , catalysis , organic chemistry , mathematical analysis , mathematics
In view of the significance of steric compression in the base‐catalyzed intramolecular cyclization of polycyclic olefinic alcohols, the standard enthalpies of formation of anti 9,10 ‐10 endo ‐hydroxytricyclo [4.2.1.1 2,5 ]deca‐3,7‐dien‐9‐one (1) and 9‐oxatetracyclo [5.4.0.0 3,10 .0 4,8 ]undec‐5‐en‐2‐one (2) as well as the kinetics of the ether formation 1 → 2 were determined.