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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 15
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Original Articles

Regiospecific Functionalization of Dimetalated (1-Naphthyl)acetylene. Efficient Synthetic Procedures for Naphtho[2,1-b]chalcophenes

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Pages 2691-2701 | Received 07 Apr 1989, Published online: 24 Oct 2006

References

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  • Brandsma , L. , Hommes , H. , Verkruijsse , H. D. and de Jong , R. L. P. 1985 . Rec. Trav. Chim. Pays-Bas , 104 : 226
  • Brandsma , L. and Verkruijsse , H. D. 1986 . Preparative Polar Organometallic Chemistry , Vol. 1 , Heidelberg : Springer-Verlag .
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  • Kulik , W. , Verkruijsse , H. D. , de Jong , R. L. P. , Hommes , H. and Brandsma , L. 1983 . Tetrahedron Lett. , 24 : 2203
  • Klusener , P. A. A. , Kulik , W. and Brandsma , L. 1987 . J. Org. Chem. , 52 : 5261
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  • Clarke , K. , Rawson , G. and Scrowston , R. M. 1969 . J. Chem. Soc. (C) , 537 The chemistry of naphtho[2,1-b]thiophene is discussed by:
  • Cagniant , P. , Close , R. , Kirsch , G. and Cagniant , D. 1975 . C. R. Acad. Sc. Paris , t. 281. Serie C : 187
  • Hanekamp , J. C. , Klusener , P. A. A. and Brandsma , L. Synth. Commun. , To be submitted
  • Hope , E. G. , Kemmitt , T. and Levason , W. 1988 . Organometallics , 7 : 78 197 – 198 . See also ref. 5
  • This solution must be clear or only slightly turbid, indicating the absence of the (unsoluble) 1:1 complex t-BuOK-t-BuOH
  • Gilman , H. and Gaj , B. J. 1957 . J. Org. Chem. , 22 : 1165 The excess of BuLi-t-BuOK reagent reacts with THF to give ethene and H2C[dbnd]CHOK, which does not interfere in the reaction with the electrophiles or chalcogenes. Compare:
  • Quenching of this mixture with Me3SiCl, gave 3 in yields higher than 80%. See ref. 1

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