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Synthesis 1993; 1993(2): 245-249
DOI: 10.1055/s-1993-25841
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Synthesis of α-Oxoketene O-Alkyl/Aryl, S-Alkyl Acetals

Makhan L. Purkayastha* , Malapaka Chandrasekharam, Jai N. Vishwakarma, Hiriyakkanavar Ila, Hiriyakkanavar Junjappa
  • *Department of Chemistry, North-Eastern Hill University Shillong 793003, Meghalaya, India
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Publication Date:
17 September 2002 (online)

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The synthesis of acylketene O,S-dialkyl acetals 2a-p and acylketene O-aryl S-alkyl acetals 6a-i is described. The compounds 2a-n are obtained by base-catalyzed alkylation of the respective β-oxo thiono esters 4a-n prepared by alkoxythiocarbonylation of active methylene ketones in the presence of sodium tert-butoxide. The corresponding O-dodecanyl 2o, O-benzyl 2p and O-aryl, S-methyl 6a-i acetals are synthesized via base-catalyzed displacement of the sulfonium salts 5a-b with the corresponding alkanol or phenol.