Gem-Difluoroallyllithium: Preparation by Lithium-Halogen Exchange and Utilization in Organosilicon and Organic Synthesis.

Abstract

GEM-Difluoroallyllithium may be generated by lithiumbromine exchange between n-butyllithium and CH2=CHCF2Br at -95 degrees C using an in situ procedure. When this Li(CF2CHCH2) preparation is carried out in the presence of chlorosilanes, aldehydes, ketones and esters, products of type R3SiCF2CH=CH2, RCH(OH)CF2CH=CH2, RR'C-(OH)CF2CH=CH, respectively, are formed, often in good yield. The factors determining the regioselectivity in additions to C=0 of unsymmetrically substituted allylic lithium reagents are discussed. (Author)

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Document Details

Document Type
Technical Report
Publication Date
Mar 23, 1983
Accession Number
ADA126094

Entities

People

  • Dennis J. Sepelak
  • Dietmar Seyferth
  • Helmut A. Klein
  • Robert M. Simon

Organizations

  • Massachusetts Institute of Technology

Tags

Communities of Interest

  • Advanced Electronics
  • Counter IED
  • Weapons Technologies

DTIC Thesaurus Topics

  • Alcohols
  • Aldehydes
  • Alkenes
  • Benzaldehydes
  • Chemical Synthesis
  • Chemistry
  • Dermatologic Agents
  • Electron Transfer
  • Electrons
  • Ethylenes
  • Films
  • Ketones
  • Low Temperature
  • Materials
  • Military Research
  • Organic Chemistry
  • Organic Compounds

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry