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The NMR spectra and conformations of cyclic compounds: IX—conformational studies of bicyclo(3,1,0)hexane derivatives by 13C NMR

✍ Scribed by Raymond J. Abraham; Collette M. Holden; Philip Loftus; David Whittaker

Publisher
John Wiley and Sons
Year
1974
Tongue
English
Weight
564 KB
Volume
6
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The ^13^C spectra of α‐thujene (1), isothujone (2), (−)isothujol (3), (+)neoisothujol (4), sabinol (5), dihydroumbellulone (6) and umbellulone (7) and the alcohol acetates are recorded and assigned. The C‐6 chemical shift may be used in conjunction with the steric shift mechanism as a conformational probe in these molecules. The results obtained indicate that isothujol, neoisothujol, isothujone and dihydroumbellulone adopt boat‐like conformations whilst sabinol has a much flatter conformation. Conjugation of the isolated double bond of α‐thujene and the carbonyl group of dihydroumbellulone with the cyclopropane ring has virtually no effect on the ^13^C shifts, but those of umbellulone itself are anomalous, indicating conjugation of the α,β unsaturated ketone system with the cyclopropyl ring.

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