A novel preparation of chlorophospholenium chlorides and their application in the synthesis of phospholene boranes

Réka Herbay, Péter Bagi, Zoltán Mucsi, Béla Mátravölgyi, L. Drahos, E. Fogassy, György Keglevich

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A novel preparation of 1-chloro-3-methyl-3-phospholenium chlorides was developed by reacting 1-substituted-3-methyl-3-phospholene 1-oxides with oxalyl chloride. The obtained cyclic chlorophosphonium salts were reacted with LiBH4to afford the corresponding 1-substituted-3-methyl-3-phospholene boranes. The latter protocol involves a silane-free deoxygenation, and borane complex formation. In one instance, a 2-phospholene borane and the corresponding P-oxide were synthesized via rearrangement of the double bond in the cyclic chlorophosphonium salt. This double bond migration was investigated by quantum chemical calculations.

Original languageEnglish
Pages (from-to)458-461
Number of pages4
JournalTetrahedron Letters
Volume58
Issue number5
DOIs
Publication statusPublished - 2017

Keywords

  • Chlorophosphonium salts
  • Deoxygenation
  • Isomerization
  • Phospholene boranes
  • Phospholene oxides
  • Quantum chemical calculations

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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