Intramolecular Ene and Related Reactions, Part 9. Photochemically Induced Synthesis of Allylsilane Carbaldehydes
- 1 January 1990
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1990 (11) , 985-990
- https://doi.org/10.1055/s-1990-27070
Abstract
Allylsilane carbaldehydes are valuable substrates for the tandem Knoevenagel allylsilane and iminium cyclization. They can easily be prepared by a photochemical α-cleavage of cyclic ketones bearing a trimethylsilylmethyl group in the α-position (Norrish Type I cleavage). The photolytic process is facilitated by the silicon due to its stabilization of a radical in the β-position. Irradiation of the ketones 15a-d leads mainly to the aldehydes 16a-d. In addition irradiation of 19a gives mostly the aldehyde 20.Keywords
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