Abstract
The 1,3-dipolar cycloaddition of diazomethane, diazoethane, phenyldiazomethane, and 2-diazopropane with several cyclobutenes, with open and cyclic cis 3,4-disubstitution, has been investigated. The cycloaddition proceeds in good yield to give syn and/or anti adducts. The structure of the adducts was established by spectroscopic data. The reactions of diazomethane cover the complete range of facial selectivity from 100% syn diastereoselectivity (e.g., with bis(mesyloxy)cyclobutene) to 100% anti diastereoselectivity (e.g., with bicyclo [3.2.0] hept-6-ene) through mixtures of various syn:anti ratios [e.g., syn:anti=60:40 with bis(methoxycarbonyl)cyclobutene]
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