The influence of exocyclic phosphorous substituents on the intrinsic stability of four-membered heterophosphetes: a theoretical study

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Abstract

Four-membered heterophosphetes such as oxaphosphetes, thiaphosphetes, and azaphosphetes have long been considered desirable target molecules for organic chemists because of their interesting structural features. In spite of extensive investigation, only one azaphosphete and one thiaphosphete have been synthesized to date. In this paper, two possible conformers of these four-membered rings, as well as their open-ring phosphorane forms with a set of exocyclic substituents and a few ring heteroatoms were studied by molecular computations. The results suggested that the relative stability of these compounds is strongly dependent on the electronic effect of the exocyclic P-substituents. Three different types of exocyclic substituents X were recognized. However, only the strong electron-withdrawing substituents (X=F, CN, OCN, SCN) were able to stabilize the ring forms, providing the possibility to design stable heterophosphetes on the basis of the present computational results.

Original languageEnglish
Pages (from-to)1868-1878
Number of pages11
JournalTetrahedron
Volume64
Issue number8
DOIs
Publication statusPublished - Feb 18 2008

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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