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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 20
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Original Articles

PTC Sulfanylation of Arylacetates

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Pages 3491-3495 | Received 17 Apr 2003, Published online: 15 Aug 2006

References

  • Trost , B.M. , Salzmann , T.N. and Hiroi , K. 1976 . New synthetic reactions—sulfenylations and dehydrosulfenylations of esters and ketones . J. Am. Chem. Soc. , 98 ( 16 ) : 4887
  • Trost , B.M. 1978 . Alpha-sulfenylated carbonyl-compounds in organic-synthesis . Chem. Rev. , 78 ( 4 ) : 363
  • Foray , G. , Peñéñory , A. and Rosi , R.A. 1997 . A novel reaction of N- phenylthiocaprolactam: the alpha-sulfenylation of ketones under mild conditions . Tetrahedron Lett. , 38 ( 12 ) : 2035
  • Wladislaw , B. , Marzorati , L. , Claro Junior , N.F. and Di Vitta , C. 1997 . A new methodology for obtaining alpha-oxo ester equivalents: sulfanylation of alpha-sulfonyl carboxylic esters in a solid/liquid phase transfer catalytic system . Synthesis , : 420
  • Wladislaw , B. , Marzorati , L. , Donnici , C.L. , Biaggio , F.C. , Neves , R.M.A. and Claro Junior , N.F. 1997 . PTC sulfanylation of some carboxylic acids derivatives activated by alpha-sulfonyl or alpha-sulfinyl group, in solid-liquid system . Phosphorus Sulfur and Silicon , 123 : 197
  • Bram , G. , Loupy , A. and Sansoulet , J. 1985 . Anionic activation by solid liquid-phase transfer catalysis without solvent—an improvement in organic-synthesis . Israel J. Chem. , 26 ( 3 ) : 291
  • In preliminary experiments, performed using liquid–liquid system (50% aq. NaOH/CH2Cl2), no sulfanylated product could be isolated, and extensive hydrolysis of the ester reagent could be observed after 24 h
  • Dou , J.M.H. , Gallo , R. , Hassanaly , P. and Metzger , J. 1977 . Behavior and stability of catalysts in biphase and triphase transfer catalysis . J. Org. Chem. , 42 ( 26 ) : 4275
  • Florac , C. , Le Grel , P. , Baudy-Floc'h , M. and Robert , A. 1991 . A facile one-pot synthesis of alpha-hydroxy acids and their derivatives . Synthesis , : 741

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