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Synthesis 2000; 2000(6): 843-849
DOI: 10.1055/s-2000-6284
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Synthesis of Symmetrical and Unsymmetrical 2,5-Bis(trialkylsilyl)furans and 2,6-Bis(trialkylsilyl)-4H-pyrans from 1,4- and 1,5-Bis(acylsilanes)

Jean-Philippe Bouillon* , Damien Saleur, Charles Portella
  • *Laboratoire "Réactions Sélectives et Applications," Associé au CNRS (UMR 6519), Université de Reims, Faculté des Sciences B.P. 1039, F-51687 Reims Cedex 2, France; Fax +33 (3) 26 91 31 66; E-mail: charles.portella@univ-reims.fr
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Publication Date:
31 December 2000 (online)

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2,5-Bis(trialkylsilyl)furans and 2,6-bis(trialkylsilyl)-4H-pyrans have been synthesized by cyclodehydration of 1,4- and 1,5-bis(acylsilanes) under p-toluenesulfonic acid catalysis. The 1,4-bis(acylsilanes) have been prepared from 1,2-bis(1,3-dithian-2-yl)ethane according to the reaction sequence metallation-silylation-dethioketalization. The 1,5-bis(acylsilanes) have been prepared from 1,3-bis(1,3-dithian-2-yl)propane by a similar strategy or from a SN reaction of 1,3-dihalopropanes with 2-trialkylsilyl-2-lithio-1,3-dithiane and deprotection. The method allows efficient preparation of symmetrical as well as unsymmetrical bis(silylated) heterocycles.

furans - 4H-pyrans - acylsilanes - cyclizations - dithianes - heterocycles