Oxidation of Organoboranes with Trimethylamine N-Oxide Dihydrate

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Recently it has been reported that the commercialy available, easily handled trimethylamine N-oxide dihydrate is an effective oxidizing agent for organoboranes. An examination of the efficiency and reactivity of this reagent under various reaction conditions was conducted. Alkenes were hydroborated to the corresponding alkylboranes, and the subsequent oxidations to alcohols were carried out using a slight excess of trimethylamine N-oxide dihydrate. The product yields at different tiem intervals were determined by glpc analysis. The oxidation can be carried out in hydrocarbon as well as ethereal solvents. The rate of oxidation is proportional to temperature. Furthermore, long reaction times at moderate temperatures are not detrimental to yields. The rates of reaction of alkyl groups in the organoborane were determined to be tertiary > cyclic secondary > acyclic secondary > n-primary > branched primary > vinyl.

Original languageEnglish (US)
Pages (from-to)273-280
Number of pages8
JournalJournal of Organometallic Chemistry
Volume125
Issue number2
DOIs
StatePublished - Feb 1 1977
Externally publishedYes

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Oxidation
oxidation
Temperature
Oxides
oxides
Alkenes
Hydrocarbons
Oxidants
Alcohols
reaction time
alkenes
Olefins
reagents
alcohols
reactivity
hydrocarbons
examination
intervals
temperature
products

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Oxidation of Organoboranes with Trimethylamine N-Oxide Dihydrate. / Kabalka, George.

In: Journal of Organometallic Chemistry, Vol. 125, No. 2, 01.02.1977, p. 273-280.

Research output: Contribution to journalArticle

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