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Synthesis 1989; 1989(6): 464-466
DOI: 10.1055/s-1989-27292
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Thiosulfonic S-Esters; 6. Fluoride-Mediated α-Phenylsulfenylation of Cyclic Ketones and Esters via their Trimethylsilyl Enol Ethers

Romualdo Caputo* , Carla Ferreri, Giovanni Palumbo
  • *Dipartimento di Chimica Organica e Biologica dell'Università, Via Mezzocannone 16, I-80134 Napoli, Italy
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Publication Date:
17 September 2002 (online)

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Ketones and carboxylic acid esters are conveniently converted to their α-sulfenylated derivatives. This new procedure is likely to represent the first reliable one for regiospecific monosulfenylation of carbonyl compounds. It is based on the reaction of their trimethylsilyl enol ether derivatives with tetrabutylammonium fluoride in the presence of thiosulfonic S-esters, in anhydrous tetrahydrofuran, under mild conditions, at - 70°C for a few minutes.