TY - JOUR
T1 - 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
AU - Tanaka, Hideo
AU - Yamashita, Shiro
AU - Yamanoue, Motoi
AU - Torii, Sigeru
PY - 1989/1/1
Y1 - 1989/1/1
N2 - 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.
AB - 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.
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U2 - 10.1021/jo00263a035
DO - 10.1021/jo00263a035
M3 - Article
AN - SCOPUS:0001233430
SN - 0022-3263
VL - 54
SP - 444
EP - 450
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -