Practical synthesis of 6-chloro-dibenzo[c.e][1,2]oxaphosphorine

Péter Abranyi-Balogh, G. Keglevich

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The title P-heterocycle 3, a versatile intermediate in synthesis, was prepared by two independent methods. The first involves an environmentally friendly version of an old protocol starting from 2-phenylphenol (1) and phosphorus trichloride. Their interaction could be accomplished at 50C under solventless conditions. Cyclization of the intermediate (2) so obtained could be realized best under microwave conditions at 150C in the presence of ZnCl2. This method offers advantages over the traditional ones. According to another approach, the chloro-dibenzooxaphosphorine (3) was obtained by the novel reaction of 6H-dibenzo[c.e][1,2]oxaphosphorine-6-oxide (4) with phosphorus trichloride in boiling chloroform. Efficiency of the syntheses was demonstrated by converting the crude product 3 to a more stable phosphonic amide (6) that was stable enough to be isolated.

Original languageEnglish
Pages (from-to)1421-1426
Number of pages6
JournalSynthetic Communications
Volume41
Issue number10
DOIs
Publication statusPublished - Jan 2011

Fingerprint

Cyclization
Chloroform
Amides
Oxides
Boiling liquids
Microwaves
phosphorus chloride
2-phenylphenol

Keywords

  • Cyclization
  • dibenzo[c.e][1,2]oxaphosphorine
  • microwave
  • substitution

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Practical synthesis of 6-chloro-dibenzo[c.e][1,2]oxaphosphorine. / Abranyi-Balogh, Péter; Keglevich, G.

In: Synthetic Communications, Vol. 41, No. 10, 01.2011, p. 1421-1426.

Research output: Contribution to journalArticle

Abranyi-Balogh, Péter ; Keglevich, G. / Practical synthesis of 6-chloro-dibenzo[c.e][1,2]oxaphosphorine. In: Synthetic Communications. 2011 ; Vol. 41, No. 10. pp. 1421-1426.
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