The synthesis of 3-phosphabicyclo[3.1.0]- hexane 3-oxides and 1,2-dihydrophosphinine 1-oxides with lipophilic p-alkoxy substituents by ring enlargement

Nõra Zsuzsa Kiss, Rõbert Örkényi, Zoltán Mucsi, György Keglevich

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Abstract

A series of 1-alkoxy-3-phospholene 1-oxides available from the microwave-assisted direct esterification of 1-hydroxy-3-phospholene oxide was converted to the two diastereomers of 6,6-dichloro-3-phosphabicyclo[3.1.0]hexane 3-oxides by the addition of dichlorocarbene to the double bond. Thermolysis of the 3-phospholene oxide-dichlorocarbene adducts afforded the corresponding 1,2-dihydrophosphinine 1-oxides as a ca. 3:1 mixture of two double bond isomers. Relative stability of the isomers of the intermediates and the products and their stereostructures were evaluated by B3LYP/6-31G(d,p) calculations.

Original languageEnglish
Pages (from-to)265-273
Number of pages9
JournalHeteroatom Chemistry
Volume25
Issue number4
DOIs
Publication statusPublished - Jul 2014

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ASJC Scopus subject areas

  • Chemistry(all)

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