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The absolute configuration of (+)-3-methyl-3-t-butyl-1-chloroallene

✍ Scribed by Ernest L. Eliel

Publisher
Elsevier Science
Year
1960
Tongue
French
Weight
161 KB
Volume
1
Category
Article
ISSN
0040-4039

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✦ Synopsis

SINCE the absolute configuration of (+)-tartaric acid was established by Bijvoet et al., 1 the configuration of any other compound containing one or more asymmetric carbons may, in principle, be established by correlation with (+)-or (-)-tartaric acid. One of the remaining general problems of static stereochemistry is the assignment of aonfiguration to optically active compounds not containing asymmetric atoms. For the case of dissymmetric biphenyls, this problem has been solved elegantly by Mislow and by Berson and their coworkers. 2 The correlation with oentroasymmetric mompounds they obtained necessarily rests on mechanistic arguments. We wish now to present a simile argument which suggests the (R)-configuration ' for (+)-+methyl-3-t-butyl-1-ohloroallene (I, Fig. 2),4 a representative of the class of dissymmetric allenes.

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