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Zur Reaktion von Pinenen mit Chlorwasserstoff
Author(s) -
Weigand Eckehard F.,
Schneider HansJörg
Publication year - 1979
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19791120826
Subject(s) - chemistry , carbocation , isomerization , hydrogen chloride , chloride , nuclear magnetic resonance spectroscopy , acetyl chloride , medicinal chemistry , photochemistry , computational chemistry , organic chemistry , catalysis
On the Reaction of Hydrogen Chloride with Pinenes syn ‐Addition of DCI to the less hindered site of α‐ and β‐pinene ( 1 , 2 ) is demonstrated by a combination of 13C‐ and 2H‐NMR spectroscopy. The resulting tertiary chloride is configurationally pure and isomerizes to bornyl chloride only. The rapidity of the isomerization with the possible conversion of a tertiary to a secondary carbocation is rationalized by strain calculations with a molecular mechanics force field.