Cycloaddition reactions of 2,2,2-trifluorodiazoethane

Abstract
2,2,2-Trifluorodiazoethane readily forms cyclopropanes when photolysed with suitable olefins. In the absence of light, a typical 1,3-dipolar addition gives Δ1-pyrazolines. This reaction, slow with ethylene, is retarded by alkyl substituents on the vinylic carbon, but accelerated slightly by halogens other than fluorine; a trifluoromethyl group has an accelerating effect of the same order of magnitude as an alkoxycarbonyl group.

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