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Carbon-13 nuclear magnetic resonance spectra of some methyl and phenyl substituted 2H-azirines

✍ Scribed by Kazuaki Isomura; Hiroshi Taniguchi; Masaaki Mishima; Mizue Fujio; Yuho Tsuno


Publisher
John Wiley and Sons
Year
1977
Tongue
English
Weight
340 KB
Volume
9
Category
Article
ISSN
0749-1581

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✦ Synopsis


Abstract

Carbon‐13 n.m.r. spectra have been obtained for some methyl and phenyl substituted 2__H__‐azirines. The higher field resonance of C‐2 than that of the corresponding aziridine carbon is interpreted in terms of ring strain. Substituent effects on the chemical shifts of the azirine ring carbons are discussed. A set of additivity parameters for the methyl and phenyl groups are obtained which can be used for the calculation of the chemical shifts of the azirine ring carbons. The substituent effect of an azirine ring on the chemical shift of benzene is also discussed in comparison with those of some other substituents. A high degree of s character (48.5%) in the exocyclic orbital of C‐3 is indicated by a large J(^13^C‐3,H) value (242.5 Hz).


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