New Functional Allylic Lithium Reagents: Gem-Dialkoxyallyllithium Reagents: A Useful Route to BETA-Silyl and beta-Stannylpropionate Esters.

Abstract

The reaction of sec-butyllithium with acrolein dialkyl acetals in THF or in THF/Et2O/pentane at -95 C results in formation of gem-dialkoxyallyllithium reagents, Li(CH2CHC(OR)2). These react with organosilicon and organotin chlorides to give ketene acetals, R3SiCH2CH=C(OR)2 and R3SnCH2CH=C(OR)2. The acid hydrolysis of these products produces beta-substituted proprionic acid esters, R3SiCH2CH2CO2R and R3SnCH2CH2CO2R. Reactions of these lithium reagents with allyl bromide gave esters of 5-hexenoic acid, CH2=CH(CH2)3CO2R (R = Me, Et). (Author)

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Document Details

Document Type
Technical Report
Publication Date
Feb 08, 1980
Accession Number
ADA081519

Entities

People

  • Dietmar Seyferth
  • Helmut A. Klein
  • Robert E. Mammarella

Organizations

  • Massachusetts Institute of Technology

Tags

Communities of Interest

  • Advanced Electronics

DTIC Thesaurus Topics

  • Acroleins
  • Aldehydes
  • Alkanes
  • Chemical Synthesis
  • Chemistry
  • Elements
  • Hydrolysis
  • Infrared Spectra
  • Materials
  • Military Research
  • New York
  • Organic Chemistry
  • Organosilicon Compounds
  • Plastic Explosives
  • Spectra
  • Standards
  • Universities

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry