Elsevier

Polyhedron

Volume 3, Issue 3, 1984, Pages 271-280
Polyhedron

The addition of methylborylene to acetylenes: Synthesis of 1,4-diboracyclohexa-2,5-dienes, and of a borirene and a diboretene derivative

https://doi.org/10.1016/S0277-5387(00)88107-3Get rights and content

Abstract

The synthesis of 1,4-dimethyl-2,3,5,6-tetra-n-alkyl-1,4-diboracyclohexa-2,5-dienes from the reaction of di-n-alkylacetylenes with the methylborylene-generating system 2C8K/MeBBr2 is described. A mechanism for these reactions is proposed. The addition of methylborylene to di-t-butylacetylene results in the formation of 1-methyl-2,3-di-t-butylborirene and of 1,3-dimethyl-2,4-di-t-butyl-1,3-diboretene.

References (41)

  • M.E. Volpin et al.

    Tetrahedron

    (1962)
  • F. Joy et al.

    J. Organometal. Chem.

    (1966)
  • J.J. Eisch et al.

    J. Organometal. Chem.

    (1979)
  • J.J. Eisch et al.

    J. Organometal. Chem.

    (1967)
  • P. Binger

    Tetrahedron Letters

    (1966)
  • G.E. Herberich et al.

    J. Organometal. Chem.

    (1978)
  • G.E. Herberich et al.

    J. Organometal. Chem.

    (1980)
  • S.M. van der Kerk et al.

    J. Organometal. Chem.

    (1980)
  • S.M. van der Kerk et al.

    J. Organometal. Chem.

    (1980)
  • S.M. van der Kerk et al.

    Angew. Chem.

    (1983)
  • P.J. Grisdale et al.

    J. Organometal. Chem.

    (1970)
  • J.J. Eisch et al.

    J. Amer. Chem. Soc.

    (1975)
  • S.M. van der Kerk

    J. Organometal. Chem.

    (1981)
  • S. M. van der Kerk and P. H. M. Budzelaar, to be...
  • H. Podall et al.

    J. Org. Chem.

    (1958)
  • W. Kuchen et al.

    Angew. Chem.

    (1960)
  • W. Kuchen et al.

    Z. Anorg. Allgem. Chem.

    (1963)
  • O.M. Nefedow et al.

    Angew. Chem.

    (1966)
  • R. Köster et al.

    Angew. Chem.

    (1966)
  • P.L. Timms

    J. Amer. Chem. Soc.

    (1967)
  • Cited by (41)

    • Borylenes as Ligands to Transition Metals

      2004, Advances in Organometallic Chemistry
    • Six-membered Rings with Two or More Heteroatoms with at least One Boron

      1996, Comprehensive Heterocyclic Chemistry II: A Review of the Literature 1982-1995
    • Boron-Carbon Multiple Bonds

      1996, Advances in Organometallic Chemistry
    View all citing articles on Scopus
    1

    Present address: Laboratory for Organic Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands.

    View full text