Cyclic phosphinates by the alkylation of a thermally unstable 1-hydroxy-1,2-dihydrophosphinine 1-oxide and A 3-hydroxy-3-phosphabicyclo[3.1.0] hexane 3-oxide

Erzsébet Jablonkai, Erika Bálint, Gyrgy T. Balogh, László Drahos, Gyrgy Keglevich

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

1-alkoxy-1,2-dihydrophosphinine oxides 4 may be prepared by the reaction of 1-hydroxy-1,2-dihydrophosphinine 1-oxide 3 with alkyl halides. The best results were obtained in boiling acetone in the presence of K 2CO 3. The outcome of the alkylation of 3-hydroxy-6,6-dichloro-3- phosphabicyclo[3.1.0]hexane 3-oxide 5 was dependent on temperature. Butylation at 56 °C in acetone using K 2CO 3 afforded mainly the expected phosphinate 6, but an increase in the temperature led to opening of the cyclopropane ring, resulting in the formation of 1-butoxy-1,2- dihydrophosphinine oxide 4a as the major product.

Original languageEnglish
Pages (from-to)357-363
Number of pages7
JournalPhosphorus, Sulfur and Silicon and the Related Elements
Volume187
Issue number3
DOIs
Publication statusPublished - Mar 1 2012

    Fingerprint

Keywords

  • 1,2-dihydrophosphinine oxide
  • 3-phosphabicyclo[3.1.0]hexane 3-oxide
  • P-heterocycles
  • phosphinates
  • phosphinic acids

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this