Photochemical decarbonylation reaction of ketones has been the focus of much interest since its discovery in the early 1900's. The mechanism of this reaction involves the loss of CO by a sequential cleavage of two sigma bonds via the Norrish Type 1 mechanism.  Our group is interested in developing the solid-state photodecarbonylation reaction to synthesize complex bicyclic compounds, carbohydrate derivatives, and functionalized cyclopentane systems  from the corresponding ketones.  Conducting the reaction in the solid state not only eliminates the need for organic solvents but it can provide stereochemical selectivities and specificities that are difficult to achieve in the standard solution state chemistry.  In addition, the success of the photodecarbonylation reaction of 1,10-dimethylcarboxylate-tetracyclo[8.8.1]nonadeca 3,5,7,12,14,16-hexa-en-19-one in the solid state producing excellent yield of the Norrish Type 1 product has prompted us to develop this reaction for inclusion in the organic chemistry laboratory curriculum.

Solid-state photodecarbonylation reaction:  Preparation of functionalized carbocyclic and carbohydrate ring systems

239th National Meeting (2010)

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