Elsevier

Tetrahedron Letters

Volume 36, Issue 19, 8 May 1995, Pages 3393-3396
Tetrahedron Letters

A direct and a formal trapping of propa-1,2-dienylidene

https://doi.org/10.1016/0040-4039(95)00490-4Get rights and content

Abstract

1,2-Dibromocyclopropene ring-opens in solution at 0 – 20 °C to give 1,2-dibromoprop-2-en-1-ylidene, which is trapped by alkenes; the derived cyclopropanes react efficiently with methyl lithium to produce eth-1-en-1-ylidenecyclopropanes. Reaction of the cyclopropene with methyl lithium in ether in the presence of an alkene leads to the same allenes by trapping of the parent allenic carbene, propa-1,2-dienylidene, albeit in low yield

1,2-Dibromocyclopropene ring-opens at 0–20 °C to 1,2-dibromoprop-2-en-1-ylidene and reacts with methyl lithium to give propa-1,2-dienylidene which is trapped by alkenes.

  1. Download : Download full-size image

References (24)

  • M.Ohishi, W.M.Irvine and N.Kaifu, Chem.Abs., 118,...G. Pineau des Forets et al.

    Mon. Nat. R. Astron. Soc.

    (1991)
  • J.M.Vrtilek, C.A.Gottlieb, T.C.Killian, P.Thaddeus, J.Cernichero, M.Guelin and G.Paubert, Chem.Abs., 118,...C.A. Gottlieb et al.

    J. Chem. Phys.

    (1993)
  • M.S. Baird et al.

    Tetrahedron Letts.

    (1985)
  • H.P. Figeys et al.

    Bull. Soc. Chim. Belges

    (1974)
    M. Kodomani et al.

    Bull. Chem. Soc. Japan

    (1989)
  • E. Hirota

    Kagaku (Kyoto)

    (1991)
  • V. Jonas et al.

    J. Phys. Chem.

    (1992)
    P. Botschwina et al.

    J. Chem. Soc., Faraday Trans.

    (1993)
    S.A. Maluendes et al.

    Chem. Phys. Lett.

    (1992)
    M.W. Wong et al.

    J. Am. Chem. Soc.

    (1993)
    R.G.A.R. Maclagan

    Theochem.

    (1992)
  • J.M. Vrtilek

    Astrophysical J.

    (1990)
    E. Herbst et al.

    Mon. Not. R. Astronom. Soc.

    (1986)
    J. Cemicharo et al.

    Astrophys. J.

    (1991)
    K. Kawaguchi et al.

    Publ. Astron. Soc. Japan

    (1991)
    M.B. Bell et al.

    Astrophysics. J., Suppl. Ser.

    (1993)
  • G. Maier et al.

    J. Am. Chem. Soc.

    (1987)
  • S. Nakamishi et al.

    Bull. Chem. Soc. Japan.

    (1992)
    M.I. Bruce

    Chem. Rev.

    (1991)
  • P.J.Stang, Alkylidenecarbenes in Carbene(oide) and Carbine, Houben-Weyl, E19b, Part 1,...
  • H.D. Hartzler

    J. Am. Chem. Soc.

    (1961)
    H.D. Hartzler

    J. Am. Chem. Soc.

    (1959)
  • M.S. Baird et al.

    J. Chem. Soc., Perkin Trans. I

    (1986)
    M.S. Baird et al.

    Tetrahedron

    (1989)

    • Cited by (16)

    View all citing articles on Scopus
    View full text
    Copyright © 1995 Published by Elsevier Ltd.