A Comparative Study of Dialkylboron Chlorides and Triflates for the Enolization of Ketones. The Controlled Stereospecific Synthesis of Either (E)- or (Z)-Enol Borinates

Abstract

The ready synthesis and ease of handling of dialkylboron chlorides, R2BC1, as compared to the corresponding triflates, R1BOTf, give the chlorides a significant advantage as reagents to achieve the conversion of ketones into enol borinates quantitatively. A systematic study, in the case of two representative ketones, propiophenone and diethyl ketone, of the effect of the steric requirement of the R group (R2 = 9-BBN vs. Chx2), the amine, Et3N vs. i-Pr2EtN, and the leaving group, Cl vs. OTf, has revealed a controlled shift from preferential (Z)-enol borinate to preferential (E)-enol borinate.

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Document Details

Document Type
Technical Report
Publication Date
May 12, 1988
Accession Number
ADA196579

Entities

People

  • Bakthan Singaram
  • Herbert C. Brown
  • Paul K. Pandiarajan
  • Raj K. Dhar
  • Raman K. Bakshi

Organizations

  • Purdue University

Tags

DTIC Thesaurus Topics

  • Abstracts
  • Alkenes
  • Amines
  • Birds
  • Boron Compounds
  • Carbon Carbon Composites
  • Chemical Synthesis
  • Chemistry
  • Chlorides
  • Ketones
  • Military Research
  • Organic Chemistry
  • Procurement
  • Security
  • United States
  • United States Government
  • Universities

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry