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Convenient Access to Bicyclic and Tricyclic Diazenes

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posted on 05.12.2008 by Douglass F. Taber, Pengfei Guo
Heating the tosylhydrazone of an ω-alkenyl ketone or aldehyde to reflux in toluene in the presence of K2CO3 delivered the bicyclic diazene. Irradiation of the diazene converted it to the cyclopropane. This appears to be a generally useful method for the construction of substituted cyclopentanes and cyclohexanes.