The formation of the benzo[f]-3-phosphabicyclo[3. 3.0]oct-6-ene ring system in the friedel-crafts reaction of the adducts of 2, 5-dihydro-1h-phosphole 1-oxides with dichlorocarbene

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Abstract

Depending on the nature of the aromatic substrate the Friedel-Crafts reaction of P-substituted 6, 6-dichloro-3-phosphabicyclo[3. 1.0]hexane 3-oxides with substituted benzenes may afford two kinds of benzo-phosphabicyclooctene derivatives as well as benzyl-phenyl-hexahydrophosphinine oxides. The formation of the tricyclic products involves the rather rarely occurring opening of the cyclopropane ring, while the benzyl-phenyl-derivatives are formed by ring expansion. Reductive type of Friedel-Crafts reaction is responsible for the formation of a part of the products. In contrast to our earlier proposal the displacement of the two chlorine atoms without the opening of the cyclopropane ring does not take place. The structure of the products was elucidated by l3C, 1H, 3lP NMR and mass spectroscopy.

Original languageEnglish
Pages (from-to)131-141
Number of pages11
JournalPhosphorus, Sulfur, and Silicon and the Related Elements
Volume63
Issue number1-2
DOIs
Publication statusPublished - Nov 1 1991

Keywords

  • Dihydrophosphole oxide-dichlorocarbene adduct
  • Friedel-Crafts reaction
  • benzo-phosphabicyclooctene oxide
  • hexahydrophosphinine oxide
  • reduction, mechanism

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Inorganic Chemistry

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