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Assignment of 13c chemical shifts in α-pinene and pinanes following catalytic deuterium exchange

✍ Scribed by David A. Forsyth; Sabri Mahmoud; Bill C. Giessen


Publisher
John Wiley and Sons
Year
1982
Tongue
English
Weight
231 KB
Volume
19
Category
Article
ISSN
0749-1581

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✦ Synopsis


Abstract

The ^13^C NMR chemical shifts of α‐pinene and cis‐ and trans‐pinanes have been reassigned on the basis of deuterium exchange experiments. Hydrogen at allylic positions in α‐pinene is exchanged for deuterium by treatment with D~2~ over an amorphous Pd‐Si alloy. Further reaction gives a mixture of pinanes labelled at four positions. The newly assigned shifts correspond well with other examples of confomationally dependent shifts in bicyclo[3.1.1]heptane derivatives.