Synthesis of(Z)-1,2-Dihalo-1-alkenes by the Reaction of (Z)-(β-Halovinyl)phenyliodonium Salts with n-Bu4NX or KX/CuX. Competition between Nucleophilic Vinylic Substitutions and Aromatic Substitutions

DOI: 10.1246/cl.1994.871

Source and publish data:

Chemistry Letters p. 871 - 874 (1994)

Update date:2022-08-04

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Authors:

Ochiai, Masahito

Oshima, Kunio

Masaki, Yukio

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Article abstract of DOI:10.1246/cl.1994.871

Nucleophilic vinylic substitutions of (Z)-(β-halovinyl)phenyliodonium salts with tetrabutylammonium halides proceed in a stereoselective manner with retention of configuration yielding vicinal (Z)-vinyl dihalides.This reaction competes with nucleophilic aromatic substitutions.Similar competition was observed in the reactions with potassium halides/cuprous halides.

Full text of DOI:10.1246/cl.1994.871

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