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Russian Chemical Bulletin

, Volume 56, Issue 8, pp 1507–1514 | Cite as

Tetraaryl-1,3-dioxolane-4,5-dimethanols as catalysts for the addition of trimethylsilyl cyanide to benzaldehyde and the oxirane ring

  • Yu. N. Belokon’
  • V. I. Maleev
  • Z. T. Gugkaeva
  • M. A. Moskalenko
  • A. T. Tsaloev
  • A. S. Peregudov
  • S. Ch. Gagieva
  • K. A. Lyssenko
  • V. N. Khrustalev
  • A. V. Grachev
Article

Abstract

The synthesis of 1,2-, 1,3-, and 1,4-phenylene-bis[(4R,5R)-4,5-di(hydroxydiphenylmethyl)-1,3-dioxolane]s (ortho-, meta-, and para-bis-(R,R)-TADDOLs) and bis[4-{[(4R, 5R)-4,5-di(hydroxydiphenylmethyl)]-1,3-dioxolan-2-yl}phenyl]methane was carried out. The possibilities of the use of these compounds as catalysts for the C-C bond formation in the addition of Me3SiCN to benzaldehyde and the oxirane ring opening in cyclohexene oxide by Me3SiCN were investigated. The catalytic activity of different bis-(R, R)-TADDOLs in this series depends on their structure.

Key words

organic catalysis Brønsted acids bis-(R,R)-α,α,α′,α ′-tetraaryl-1,3-dioxolane-4,5-dimethanols mandelonitrile trimethylsilyl cyanide 

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Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • Yu. N. Belokon’
    • 1
  • V. I. Maleev
    • 1
  • Z. T. Gugkaeva
    • 1
  • M. A. Moskalenko
    • 1
  • A. T. Tsaloev
    • 1
  • A. S. Peregudov
    • 1
  • S. Ch. Gagieva
    • 1
  • K. A. Lyssenko
    • 1
  • V. N. Khrustalev
    • 1
  • A. V. Grachev
    • 1
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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