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Synthesis 1990; 1990(11): 985-990
DOI: 10.1055/s-1990-27070
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Intramolecular Ene and Related Reactions, Part 9. Photochemically Induced Synthesis of Allylsilane Carbaldehydes

Lutz F. Tietze* , Josef R. Wünsch
  • *Institut für Organische Chemie der Universität Göttingen, Tammannstraße 2, D-3400 Göttingen, Germany
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Publication Date:
17 September 2002 (online)

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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.