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Synthesis 1995; 1995(6): 654-658
DOI: 10.1055/s-1995-3976
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Addition of 2-(Trimethylsilyl)thiazole to Alkyl and Aryl Perfluoroalkyl Ketones: Synthesis of Fluorinated Tertiary Alcohols and α-Hydroxy Aldehydes

Alessandro Dondoni* , Alessia Boscarato, Paolo Formaglio, Jean-Pierre Bégué, Farid Benayoud
  • *Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, I-44100 Ferrara, Italy, Fax +39(532)240709
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Publication Date:
31 December 2000 (online)

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The spontaneous addition of 2-(trimethylsilyl)thiazole (2-TST, 1) to various alkyl and aryl perfluoroalkyl ketones 2 in THF at 80°C affords the corresponding tertiary alcohols 4 which by thiazolyl-to-formyl conversion are transformed into fluorinated α-hydroxy aldehydes 6. The formation of silyl enol ether side products is observed in the reaction of 2-TST 1 with alkyl ketones 2b-e.

2-(trimethylsilyl)thiazole - fluoro ketones - α-hydroxy aldehydes - carbonyl addition - homologation