Takaaki Kakinami

An effective chlorinating agent benzyltrimethylammonium tetrachloroiodate, benzylic chlorination of alkylaromatic compounds☆

Abstract The reaction of alkylaromatic compounds with benzyltrimethylammonium tetrachloroiodate in carbon tetrachloride in the presence of AIBN under reflux for several hours gave α-chloro-substituted compounds in fairly good yields.

Halogenation using quaternary ammonium polyhalides. Part 22. Selective bromination of aromatic ethers with benzyltrimethylammonium tribromide

The reaction of aromatic ethers with a stoicheiometric amount of benzyltrimethylammonium tribromide in dichloromethane–methanol or acetic acid–ZnCl2 under mild conditions gave, selectively, mono-, di-, or tri-bromo-substituted aromatic ethers in quantitative yields.

Ultrasound-assisted reduction of cyanides to deuteriated aliphatic amines

In the presence of ultrasound various mono-, di-, and α,β-unsaturated cyanides were reduced with Cu-Al alloy in NaOD-D 2 O and THF to the corresponding deuteriated aliphatic amines, such as nonylamines, Putrescine, and 1,6-hexanediamine, in high deuterium content.

Bromination and oxidation with benzyltrimethylammonium tribromide

Abstract Our recent studies on effective bromination and oxidation using benzyltrimethylammonium tribromide (BTMA Br 3 ), stable solid, are described. Those involve electrophilic bromination of aromatic compounds such as phenols, aromatic amines, aromatic ethers, acetanilides, arenes, and thiophene, α-bromination of arenes and acetophenones, and also bromo-addition to alkenes by the use of BTMA Br 3 . Furthermore, oxidation of alcohols, ethers, 1,4-benzenediols, hindered phenols, primary amines, hydrazo compounds, sulfides, and thiols, haloform reaction of methylketones, N-bromination of amides, Hofmann degradation of amides, and preparation of acylureas and carbamates by the use of BTMA Br 3 are also presented.

Facile synthesis of N-bromoamides using benzyltrimethylammonium tribromide in alkaline solution

Aliphatic and aromatic amides reacted with a stoicheiometric amount of benzyltrimethylammonium tribromide in ice-cold aqueous sodium hydroxide to give N-bromoamides in good yields.