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Carbon-13 NMR analysis of cyclobutane dimers from benzocycloalkenes

✍ Scribed by C. E. Browne; P. H. Ruehle; T. K. Dobbs; E. J. Eisenbraun

Publisher
John Wiley and Sons
Year
1979
Tongue
English
Weight
376 KB
Volume
12
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

^13^C NMR Spectra for a series of 11 substituted cyclobutanes derived from photodimerization of benzocycloalkenes were recorded. Comparison of the carbon chemical shifts for the head‐to‐head and head‐to‐tail cis‐syn‐cis and cis‐anti‐cis isomers reveals shielding trends which should facilitate structural and stereochemical assignments for related compounds. The head‐to‐head isomers show a larger separation of cyclobutane carbon resonances than the head‐to‐tail isomers. The cis‐syn‐cis isomers relative to the cis‐anti‐cis isomers exhibit distinctive upfield shifts of all carbon resonances, except those of aromatic carbons ortho to alkyl‐substituted aromatic carbons.

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