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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 9, 1979 - Issue 10
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Original Articles

α-Methylthiocarbonylation of Ketones. Generality and Regioselectivity

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Pages 883-888 | Received 20 Jun 1979, Published online: 06 Dec 2006

References

  • To whom correspondence should be addressed
  • Demuynck , C. and Thuillier , A. 1969 . Bull. Soc. Chim. , : 2434
  • Liu , H. J. and Lai , H. K. 1979 . Tetrahedron Lett. , : 1193
  • S,S'-Dimethyl dithiocarbonate, b.p. 75°C/10 Torr, was prepared in 50% yield by rearrangement5 of S-methyl methyl xanthate with 0.5 eq AlCl3 in refluxing CS2 for 3 hr. For another method, see ref. 6
  • Kawata , T. and Muro , T. Japan Kokai 74 70926 . 1974 . Chem. Abstr., 81, 119942w (1974)
  • Pelster , H. and Muehlbauer , E. Ger. Patent 1181205 . 1964 . Chem. Abstr., 62, 6398c (1965)
  • All new compounds were adequately characterized by spectroscopic methods and by exact mass measurement and/or elemental analysis. Most products exist partially in the corresponding enol form
  • The reaction was carried out using 1.5 eq of S,S'-dimethyl dithiocarbonate
  • This compound exists completely in the enol form. The structure was confirmed by oxidation with DDQ in refluxing benzene to the corresponding 1,2-dehydro derivative

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