Reductive addition of polyhalomethanes and their related compounds to aldehydes and 1,2-elimination of the coupling products in a Pb/Al bimetal redox system

Hideo Tanaka, Shiro Yamashita, Motoi Yamanoue, Sigeru Torii

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

A Pb/Al bimetal system was used to carry out reductive addition of tetrachloromethane, tetrabromomethane, bromotrichloromethane, trichloroacetamide, and trichloroacetonitrile to aldehydes. Subsequent 1,2-elimination of the halogen atom and hydroxyl group from the coupling products was also performed with the Pb/Al bimetal system. The technology was successfully applied to stereocontrolled syntheses of ethyl trans- and cis-3-(2,2-dihaloethenyl)-2,2-dimethylcyclopropanecarboxylates.

Original languageEnglish
Pages (from-to)444-450
Number of pages7
JournalJournal of Organic Chemistry
Volume54
Issue number2
Publication statusPublished - 1989

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Bimetals
Aldehydes
Bromotrichloromethane
Halogens
Carbon Tetrachloride
Hydroxyl Radical
Atoms
Oxidation-Reduction
trichloroacetonitrile
trichloroacetamide
carbon tetrabromide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Reductive addition of polyhalomethanes and their related compounds to aldehydes and 1,2-elimination of the coupling products in a Pb/Al bimetal redox system. / Tanaka, Hideo; Yamashita, Shiro; Yamanoue, Motoi; Torii, Sigeru.

In: Journal of Organic Chemistry, Vol. 54, No. 2, 1989, p. 444-450.

Research output: Contribution to journalArticle

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