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1H NMR spectra of oxiranes. cis-Arylmethyl oxiranes substituted in the phenyl ring

✍ Scribed by L. Villa; L. Schenetti; F. Taddei

Book ID
102528200
Publisher
John Wiley and Sons
Year
1973
Tongue
English
Weight
258 KB
Volume
5
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The ^1^H NMR parameters for a number of cis‐arylmethyl oxiranes are reported and discussed in comparison with those of trans derivatives and styrene oxides substituted in the phenyl ring. While the macroscopic behaviour of the results is in agreement with a perturbative mechanism through the oxirane ring that is mainly electrostatic in character, a small contribution due to conjugative interaction is not excluded. It seems likely that the effect of substituents in the phenyl ring is mainly transmitted through bonds rather than through space, and that the different polarisation of the CH bonds in the oxirane ring is mainly responsible for the different behaviour of the protons in cis‐ and trans‐ arylmethyl oxiranes towards the effect of substituents.

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