Russian Chemical Bulletin

, Volume 42, Issue 10, pp 1709–1712 | Cite as

Hydrosilylation of unsaturated compounds with 5-dimethylsilylfurfural diethyl acetal

  • E. Lukevics
  • L. E. Demicheva
  • N. P. Yerchak
  • Yu. Popelis
Organic Chemistry

Abstract

Hydrosilylation of terminal acetylenes, HC≡CR (R = CMe3,n-C7H15, SiMe3, Ph, COOEt, CH2N(CH2)4, and CH2N(CH2)5) with 5-dimethylsilylfurfural diethyl acetal (1) gives a mixture of products of bothtrans-β- and α-addition. When R = CMe3 or SiMe3, the reaction proceeds regio- and stereospecifically to give only thetrans-β-derivatives. The formation of β-adducts is favored by pronounced electron-donating substituents and steric hindrance at the Cα atom. Terminal alkenes, H2C=CHR (R = CH2CN, CH2N(CH2)4, CH2N(CH2)5, SiMe3, SiMe(α-furyl)2, SiMe2(α-furyl), SiMe2(α-thienyl), and SiMe2(5-chloro-2-thienyl)), react with silane1 to give only the products of β-addition; the reaction of1 with H2C=CHCH2NHC6H13-n affords a mixture of β- and α-adducts in a ratio of 1.8∶1.

Key words

hydrosilylation 5-dimethylsilylfurfural diethyl acetal terminal acetylenes and alkenes regioselectivity 

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Copyright information

© Plenum Publishing Corporation 1994

Authors and Affiliations

  • E. Lukevics
    • 1
  • L. E. Demicheva
    • 1
  • N. P. Yerchak
    • 1
  • Yu. Popelis
    • 1
  1. 1.Institute of Organic SynthesisLatvian Academy of SciencesRigaLatvia

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