The First Delocalized Phosphole Containing a Planar Tricoordinate Phosphorus Atom: 1-[Bis(trimethylsilyl)methyl]-3,5-bis(trimethylsilyl)-1,2,4-triphosphole

F Geoffrey N Cloke; Peter B Hitchcock; Philip Hunnable; John F Nixon; Lászlo Nyulászi; Edgar Niecke; Vera Thelen

doi:10.1002/(SICI)1521-3773(19980504)37:8<1083::AID-ANIE1083>3.0.CO;2-C

The First Delocalized Phosphole Containing a Planar Tricoordinate Phosphorus Atom: 1-[Bis(trimethylsilyl)methyl]-3,5-bis(trimethylsilyl)-1,2,4-triphosphole

Angew Chem Int Ed Engl. 1998 May 4;37(8):1083-1086. doi: 10.1002/(SICI)1521-3773(19980504)37:8<1083::AID-ANIE1083>3.0.CO;2-C.

Authors

F Geoffrey N Cloke¹, Peter B Hitchcock¹, Philip Hunnable¹, John F Nixon¹, Lászlo Nyulászi², Edgar Niecke³, Vera Thelen³

Affiliations

¹ School of Chemistry, Physics and Environmental Sciences, University of Sussex, Brighton, Sussex, BN1 9QJ (UK), Fax: (+44) 1273-677196.
² Department of Inorganic Chemistry, Technical University of Budapest, H-1521 Budapest, Gellert ter 4 (Hungary).
³ Anorganisch-Chemisches Institut der Universitat, Gerhard-Domagk-Strasse 1, D-53121 Bonn (Germany).

Abstract

The sterically demanding groups on the tricoordinate phosphorus atom, the π-electron acceptors substituted on the ring, and the dicoordinate phosphorus atoms within the ring are the most significant factors contributing to the planarity and aromaticity of the 1,2,4-triphosphole ring in 1. The Bird aromaticity index for 1 shows that it has the most pronounced aromatic character of all known phospholes.

Keywords: Aromaticity; Heterocycles; Phospholes; Phosphorus.