syn–anti-Isomerism in the cycloaddition of nitrile oxides to cis-3,4-dichlorocyclobutene
- 1 January 1974
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 137-140
- https://doi.org/10.1039/p19740000137
Abstract
1,3-Dipolar cycloaddition reactions of cis-3,4-dichlorocyclobutene with several nitrile oxides yield mixtures of syn- and anti- 4-substituted 6,7-dichloro-2-oxa-3-azabicyclo[3.2.0]hept-3-enes. The structures of the cycloadducts are deduced from n.m.r. and dipole moment data and a possible explanation for the abnormally high proportion of the sterically disfavoured syn-isomer is presented.Keywords
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