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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 4
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Original Articles

Reductive Lithiation of Some Thioketals Using Lithium 1-(Dimethylamino)naphthalenide

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Pages 311-317 | Published online: 06 Dec 2006

References

  • Cohen , T. , Daniewski , W. M. and Weisenfeld , R. B. 1978 . Tetrahedron Lett. , : 4665
  • Cohen , T. and Weisenfeld , R. B. 1979 . J. Org. Chem. , 44 : 3601
  • Cohen , T. , Gapinski , R. E. and Hutchins , R. 1979 . J. Org. Chem. , 44 : 3599
  • Screttas , C. G. and Micha-Screttas , M. 1979 . J. Org. Chem. , 44 : 713 Screttas and Micha-Screttas have reported the reductive lithiation with this reagent of a number of simple thioethers and of pentanal bis(phenylthio)acetal, albeit at somewhat higher temperatures than were used by us, ibid., 43, 1064 (1978)
  • Angelo , B. 1968 . Bull. Soc. Chim. Fr. , : 3855 The development of paramagnetism was reported when lithium was mixed with 7 in THF at room temperature; however, our experience indicates that the paramagnetism was probably due to transient 3.
  • The stability of the reducing agent above -45° in the catalytic procedure may be due to the far shorter average lifetime of the radical anions or to the absence of the dianion which could be the species that loses the dimethylamide anion
  • In the catalytic method, completion of reduction can be readily determined visually; the dark red color of the sulfur-stabilized anion is replaced by the green-black color of the radical anion
  • Posner , G. H. , Whitten , C. E. and Sterling , J. J. 1973 . J. Am. Chem. Soc. , 95 : 7788

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