Why are phosphole oxides unstable? The phenomenon of antiaromaticity as a destabilizing factor

Zoltán Mucsi, György Keglevich

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17 Citations (Scopus)

Abstract

It is shown that the great instability of phosphole oxides can be attributed to their antiaromatic characters. The aromatic-antiaromatic switch in the course of the oxidation of phospholes, which may be fine-tuned by P substituents, increases the reactivity toward dimerisation, leading to the corresponding 7-phosphanorbornene rings. The degree of antiaromaticity of these stable compounds is examined and quantified on a linear aromatic and antiaromatic scale.

Original languageEnglish
Pages (from-to)4765-4771
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number28
DOIs
Publication statusPublished - Oct 19 2007

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Keywords

  • Ab initio DFT calculations
  • Antiaromaticity
  • Aromaticity scale
  • Phosphole oxide

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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