Photoreactivity of 3-thujopsanone

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Abstract

The photoreactivity in the liquid phase of the polysubstituted cyclohexanones 3-thujopsanones results from a primary process of Norrish I type, but is modified by the opening of the cyclopropyl ring. Quantum yields are higher than for less substituted cycloalkanones. In aprotic solvents, only hydrocarbons are formed either with the loss of a C2H2O group leading to the main photoproduct 4 or with decarbonylation of the ketone leading to a new cyclopropyl chain. In alcohol solvent, two isomeric compounds with an oxygenated heterocycle are obtained from the addition of solvent to a carbene intermediate.

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