Synthesis of α,α-dichloroalcohols, α-hydroxyketones and 1-chloro-1-arylalkylene oxides via protonation of acyllithium reagents

George Kabalka, Nan Sheng Li, Su Yu

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The protonation of acyllithium reagents generated in situ from alkyllithiums and carbon monoxide in the presence of dichloromethane or dichloroarylmethanes produces α,α-dichloroalcohols in high yields. The reaction produces α-hydroxy-ketones in high yields when the aryl group of dichloroarylmethane contains a strong electron-donating group at the ortho or para position. The transformation of α,α-dichloro-α-aryl alcohols into 1-chloro-1-arylalkylene oxides is achieved in high yields by using sodium amide as a base.

Original languageEnglish (US)
Pages (from-to)31-36
Number of pages6
JournalJournal of Organometallic Chemistry
Volume572
Issue number1
DOIs
StatePublished - Jan 5 1999

Fingerprint

Methylene Chloride
Protonation
Dichloromethane
Carbon Monoxide
Ketones
Amides
Carbon monoxide
Oxides
reagents
Alcohols
Sodium
Electrons
oxides
synthesis
ketones
carbon monoxide
amides
alcohols
sodium
electrons

All Science Journal Classification (ASJC) codes

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

Cite this

Synthesis of α,α-dichloroalcohols, α-hydroxyketones and 1-chloro-1-arylalkylene oxides via protonation of acyllithium reagents. / Kabalka, George; Li, Nan Sheng; Yu, Su.

In: Journal of Organometallic Chemistry, Vol. 572, No. 1, 05.01.1999, p. 31-36.

Research output: Contribution to journalArticle

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abstract = "The protonation of acyllithium reagents generated in situ from alkyllithiums and carbon monoxide in the presence of dichloromethane or dichloroarylmethanes produces α,α-dichloroalcohols in high yields. The reaction produces α-hydroxy-ketones in high yields when the aryl group of dichloroarylmethane contains a strong electron-donating group at the ortho or para position. The transformation of α,α-dichloro-α-aryl alcohols into 1-chloro-1-arylalkylene oxides is achieved in high yields by using sodium amide as a base.",
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