Enolboration 3. An Examination of the Effect of Variable Steric Requirements of R on the Stereoselective Enolboration of Ketones with R2BCl/Et3N. Bis(Bicyclo(2.2.2)Octyl)Chloroborane/Triethylamine - A New Reagent Which Achieves the Selective Generation of E Enolborinates from Representative Ketones

Abstract

A smooth, rapid, quantitative and stereoselective enolboration of a variety of ketones to E enolborinates is achieved with bis(bicyclo2.2.2octyl) chloroborane, Bco2BC1, a new reagent, in the presence of triethylamine, in simple solvents, such as diethyl ether, hexane, carbon tetrachloride, and methylene chloride. Representative R2BC1 reagents with variable steric requirements have been examined, with 3-pentanone and propiophenone as model ketones, in order to understand the effect of the steric requirements of R in controlling the enolate geometry.

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Document Details

Document Type
Technical Report
Publication Date
Apr 28, 1992
Accession Number
ADA250066

Entities

People

  • H. C. Brown
  • K. Ganesan
  • R. K. Dhar

Organizations

  • Purdue University

Tags

Communities of Interest

  • Weapons Technologies

DTIC Thesaurus Topics

  • Alcohols
  • Alkenes
  • Benzaldehydes
  • Chemical Shifts
  • Chemical Synthesis
  • Chemistry
  • Chlorides
  • Ketones
  • Military Research
  • Organic Chemistry
  • Precipitation

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry