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Carbon‐13 chemical shifts of bicyclo[3.2.1]octane and bicyclo[2.2.1]heptane derivatives
Author(s) -
Lippmaa E.,
Pehk T.,
Belikova N. A.,
Bobyleva A. A.,
Kalinichenko A. N.,
Ordubadi M. D.,
Platé A. F.
Publication year - 1976
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270080204
Subject(s) - bicyclic molecule , heptane , octane , chemistry , steric effects , substituent , ring (chemistry) , stereochemistry , medicinal chemistry , organic chemistry
Abstract 13 C chemical shifts of more than fifty bicyclo[3.2.1]octane and bicyclo[2.2.1]heptane derivatives (hydrocarbons, alcohols, ketones and esters) have been determined. The usefulness of ethyl derivatives for the assignment of close 13 C chemical shifts in bicyclic methyl derivatives is shown both for the bicyclo[3.2.1]octane and bicyclo[2.2.1]heptane series. Comparison of substituent effects on α‐, β‐, γ‐ and δ‐carbons in both series of compounds shows remarkable differences in steric interactions. In contrast to the rigid bicyclo[2.2.1]heptane system, both chair and boat conformations can be predominant in the bicyclo[3.2.1]octane series with the conformationally flexible 6‐membered ring.