Facile synthesis of 1, 2, 3, 4, 5, 6- hexahydrophosphinine 1-oxides by the hydrogenation of 1, 2-dihydrophosphinine 1-oxides

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Abstract

The hydrogenation of the dihydrophosphinine oxides obtained from 3-methyl- or 3, 5-dimethy1-1-alkoxy-2, 5-dihydro-1H-phosphole oxides on ring enlargement gives the diastereoisomers of new hexahydrophosphinine oxides. Conformational analysis of the 3-methyl-products suggests the equilibria to be strongly biased toward structures with an equatorial C-methyl substituent. In contrast, the predominant diastereoisomer of the 3, 5-dimethyl-product exists as an equilibrium of two conformers. A new P-chloro-hexahydrdophosphinine has also been prepared from the ethoxy-derivative which is useful in the synthesis of the amino-product. The hexahydrophosphinine oxides are characterized by 31P, l3C and 1H NMR and mass spectroscopic methods.

Original languageEnglish
Pages (from-to)219-227
Number of pages9
JournalPhosphorus, Sulfur, and Silicon and the Related Elements
Volume70
Issue number1-4
DOIs
Publication statusPublished - Jan 1 1992

Keywords

  • Conformer
  • Dihydrophosphinine oxide
  • diastereoisomer
  • hexahydrophosphinine oxide
  • hydrogenation
  • stereospecific coupling

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Inorganic Chemistry

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