New P-ligands: The aromaticity and reactivity of 2,4,6- trialkylphenylphospholes

György Keglevich, Renáta Farkas, Krisztina Ludányi, Veronika Kudar, Miklós Hanusz, Kálmán Simon

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Abstract

A further member of 2,4,6-trialkyl-phenylphospholes, the ditertbutylmethylphenyl derivative (1c) was characterized by Bird index and by the sum of angles at the phosphorus atom to describe the flattening of the P-pyramid. Both numbers suggested a slight aromaticity. The reaction of arylphospholes with phosphorus tribromide was extended to phosphole 1c leading this occasion, after further steps, to the mixture of 3- and 2-substituted products (3c-1 and 3c-2, respectively). A triisopropylphenyl-2H-phosphole (4) formed by sigmatropic rearrangement was utilized in the preparation of new 1-phosphanorbornene derivatives, such as sulfide 6 and hemi-oxides 8-1 and 8-2. Further oxidation of the latter species (8-1 and 8-2) led to the decomposition of the dimeric structure (11). 4 could also be trapped by benzaldehyde to afford the oxaphosphanorbornene (10) as one diastereomer. Finally, the reversible formation of 2H-phosphole 4 from 1H-phosphole 1a at 150°C was proved.

Original languageEnglish
Pages (from-to)104-110
Number of pages7
JournalHeteroatom Chemistry
Volume16
Issue number2
DOIs
Publication statusPublished - May 6 2005

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ASJC Scopus subject areas

  • Chemistry(all)

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