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Convenient access to bicyclic and tricyclic diazenes.

ABSTRACT: Heating the tosylhydrazone of an omega-alkenyl ketone or aldehyde to reflux in toluene in the presence of K(2)CO(3) 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.

SUBMITTER: Taber DF

PROVIDER: S-EPMC2765546 | biostudies-literature | 2008 Dec

REPOSITORIES: biostudies-literature

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Convenient access to bicyclic and tricyclic diazenes.

Taber Douglass F DF Guo Pengfei P

The Journal of organic chemistry 20081201 23

Heating the tosylhydrazone of an omega-alkenyl ketone or aldehyde to reflux in toluene in the presence of K(2)CO(3) 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. ...[more]

PMID: 18980330

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