Elsevier

Tetrahedron Letters

Volume 37, Issue 37, 9 September 1996, Pages 6665-6668
Tetrahedron Letters

Stopping the aromatic ring current. Synthesis of the first bis-metal complexed benzannulene. On the way to a molecular conductor with a photo-switch

https://doi.org/10.1016/S0040-4039(96)01491-8Get rights and content

Abstract

The mild ligand exchange reaction between (tricarbonylchromium)naphthalene and the dibenzannulene 4 permits synthesis of the first bis-complexed large ring benzannulene 5. Progressive reduction of the strong ring current of 1 occurs in going from 1–5, which in the latter is only about 6% of that in 1.

Bis complexation of 4 can be achieved in 80% yield using (tricarbonylchromium)naphthalene to give mostly isomer 5. The ring current of the latter is only 6% of that of 1.

  1. Download : Download full-size image

References (13)

  • R.C. Haddon

    Tetrahedron

    (1972)
    R.H. Mitchell

    Adv. in Theoret. Interesting Molec.

    (1989)
  • R. Neidlein et al.

    Helv. Chim. Acta

    (1994)
    D. Solooki et al.

    Organometallics

    (1994)
    D. Solooki et al.

    J. Orgmet. Chem.

    (1994)
  • R.H. Mitchell et al.

    J. Am. Chem. Soc.

    (1982)
    R.H. Mitchell et al.

    J. Am. Chem. Soc.

    (1982)
  • R.H. Mitchell et al.

    J. Am. Chem. Soc.

    (1995)
  • R.H. Mitchell et al.

    J. Am. Chem. Soc.

    (1990)
  • R. Gompper et al.

    Tetrahedron Lett.

    (1992)
    L. Giannini et al.

    Angew. Chem. Int. Ed. Engl.

    (1994)
There are more references available in the full text version of this article.

Cited by (0)

View full text
Copyright © 1996 Published by Elsevier Ltd.