Synthesis and Reactivity of a New (Methylene)Phosphine.

Abstract

A new, stable (methylene)phosphine (Me3Si)2N-P=CHsiMe3 (4) was prepared via dehydrohalogenation of the chlorophosphine, (Me3Si)2N-P(Cl)-CH2SiMe3 (1), using LiN(SiMe3)2 as the base. Compound 1 and the related phosphine, (Me3Si)2NP(CH2SiMe3)2 (2), were obtained by treating (Me3Si)2NPCl2 with either one or two equivalents of Me3SiCH2MgCl. Reaction of 1 with t-BuLi proceeded via chloride displacement rather than dehydrohalogenation to afford the t-butylphosphine, (Me3Si)2NP(t-Bu)CH2SiMe3 (3). Two different modes of reactivity of 4 were observed: methanol added to the p pi bond yielding the methoxyphosphine, (Me3Si)2NP(OMe)CH2SiMe3 (5), while treatment with Me3SiN3 gave the novel imino (methylene)phosphorane, (Me3Si)2NP(=NSiMe3) (=CHSiMe3) (6). Compound 6 also added methanol to form a P-methoxyphosphinimine, (Me3Si)2NP(OMe) (=NSiMe3)CH2SiMe3 (7).

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Document Details

Document Type
Technical Report
Publication Date
Jan 27, 1981
Accession Number
ADA094885

Entities

People

  • Robert H. Neilson

Organizations

  • Texas Christian University

Tags

Communities of Interest

  • Advanced Electronics
  • C4I

DTIC Thesaurus Topics

  • Alcohols
  • Chemical Compounds
  • Chemical Synthesis
  • Chemistry
  • Christianity
  • Classification
  • Distillation
  • Elements
  • Inorganic Chemistry
  • Isomers
  • Methanols
  • Military Research
  • New York
  • Organophosphorus Compounds
  • Phosphorus Compounds
  • Spectra
  • United States

Fields of Study

  • Chemistry

Readers

  • Military Logistics and Supply Chain Management
  • Organic Chemistry