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 journalArticlepeer-review

46 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
DOIs
Publication statusPublished - Jan 1 1989

ASJC Scopus subject areas

  • Organic Chemistry

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