P‐Substituted 3‐phosphabicyclo [3.1.0] hexane 3‐oxides from diastereoselective substitution at phosphorus

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Abstract

Preparation of P‐amino‐3‐phosphabicyclo[3.1.0]‐hexane 3‐oxides either by addition of dichlorocarbene to the double bond of 1‐amino‐2,5‐dihydro‐1H‐phosphole 1‐oxides or by substitution of the P‐chloro derivative of the bicyclic system was accomplished. Two different diastereomers are obtained by the two approaches; their 13C NMR spectra were interpreted on the basis of the P‐ethoxy isomers, whose structures were confirmed by X‐ray analysis. The P‐hydroxy adduct was also prepared, and it was found that intermolecular OH … O hydrogen bonding connects the molecules together in the solid phase. This effect eliminates the possibility of diastereoisomerism, as was also observed in the case of P‐hydroxy tetrahydrophosphinine oxides. Thermolysis of the P‐hydroxy adduct is a better way to synthesize 1‐hydroxy‐1,2‐dihydrophosphinine oxides than by hydrolysis of the phosphinic chlorides.

Original languageEnglish
Pages (from-to)329-335
Number of pages7
JournalHeteroatom Chemistry
Volume4
Issue number4
DOIs
Publication statusPublished - 1993

ASJC Scopus subject areas

  • Chemistry(all)

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