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13C NMR spectra of cyclopropane derivatives. Stereoisomeric substituted 2-phenylcyclopropanes

✍ Scribed by O. A. Subbotin; A. S. Kozmin; Yu K. Grishin; N. M. Sergeyev; I. G. Bolesov

Publisher
John Wiley and Sons
Year
1972
Tongue
English
Weight
477 KB
Volume
4
Category
Article
ISSN
0749-1581

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✦ Synopsis

Proton-decoupled carbon-1 3 magnetic resonance spectra of a series of cyclopropane derivatives have been studied. For stereoisomeric substituted 2-phenylcyclopropanes a difference between the isomers has been found in the shieldings of the three-membered cyclic carbons as well as in the shieldings of the carbons of the substituents. The chemical shifts have been interpreted on the basis of an additive approach worked out in a study of the spectra of monosubstituted cyclopropanes and substituted 2,2-diphenylcyclopropanes. Some simple rules have been proposed, which are useful in distinguishing stereoisomeric 1,2-disubstituted cyclopropanes.

* Except for 2,2-diphenylcyclopropylamine (14), which was obtained as a crystalline compound for the first time in this work. Elemental analyses of 14, the hydrochloride and the benzoyl derivative are in good agreement with the calculated values.

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