Electrogenerated Base (EG Base) Induced Hydroxymethylation of the Side Chain of Nitroalkylbenzenes with Paraformaldehyde

Sigeru Torii; Yasuo Murakami; Hideo Tanaka; Koichi Okamoto

doi:10.1021/jo00366a012

Electrogenerated Base (EG Base) Induced Hydroxymethylation of the Side Chain of Nitroalkylbenzenes with Paraformaldehyde

Sigeru Torii, Yasuo Murakami, Hideo Tanaka, Koichi Okamoto

Faculty of Engineering

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

Hydroxymethylation of nitroalkylbenzenes with paraformaldehyde was accomplished by electrolysis in a (CH₂O)_n–DMF–Et₄NOTs–(Pt electrode) system. The reaction was found to be catalytic (0.25 faraday/mol) and dependent on the electroreduction of formaldehyde and/or nitroalkylbenzene. A variety of nitroalkylbenzenes were transformed to their corresponding mono- and/or bishydroxymethylated derivatives in good yield. The product yield and selectivity were shown to depend on the order of reagent addition, solvent, supporting electrolyte, and structure of the starting nitroalkylbenzenes. A plausible mechanism of the generation of base catalysts (EG base) in electroreductive media is discussed.

Original language	English
Pages (from-to)	3143-3147
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	51
Issue number	16
DOIs	https://doi.org/10.1021/jo00366a012
Publication status	Published - 1986

ASJC Scopus subject areas

Organic Chemistry

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title = "Electrogenerated Base (EG Base) Induced Hydroxymethylation of the Side Chain of Nitroalkylbenzenes with Paraformaldehyde",

abstract = "Hydroxymethylation of nitroalkylbenzenes with paraformaldehyde was accomplished by electrolysis in a (CH2O)n–DMF–Et4NOTs–(Pt electrode) system. The reaction was found to be catalytic (0.25 faraday/mol) and dependent on the electroreduction of formaldehyde and/or nitroalkylbenzene. A variety of nitroalkylbenzenes were transformed to their corresponding mono- and/or bishydroxymethylated derivatives in good yield. The product yield and selectivity were shown to depend on the order of reagent addition, solvent, supporting electrolyte, and structure of the starting nitroalkylbenzenes. A plausible mechanism of the generation of base catalysts (EG base) in electroreductive media is discussed.",

author = "Sigeru Torii and Yasuo Murakami and Hideo Tanaka and Koichi Okamoto",

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T1 - Electrogenerated Base (EG Base) Induced Hydroxymethylation of the Side Chain of Nitroalkylbenzenes with Paraformaldehyde

AU - Torii, Sigeru

AU - Murakami, Yasuo

AU - Tanaka, Hideo

AU - Okamoto, Koichi

PY - 1986

Y1 - 1986

N2 - Hydroxymethylation of nitroalkylbenzenes with paraformaldehyde was accomplished by electrolysis in a (CH2O)n–DMF–Et4NOTs–(Pt electrode) system. The reaction was found to be catalytic (0.25 faraday/mol) and dependent on the electroreduction of formaldehyde and/or nitroalkylbenzene. A variety of nitroalkylbenzenes were transformed to their corresponding mono- and/or bishydroxymethylated derivatives in good yield. The product yield and selectivity were shown to depend on the order of reagent addition, solvent, supporting electrolyte, and structure of the starting nitroalkylbenzenes. A plausible mechanism of the generation of base catalysts (EG base) in electroreductive media is discussed.

AB - Hydroxymethylation of nitroalkylbenzenes with paraformaldehyde was accomplished by electrolysis in a (CH2O)n–DMF–Et4NOTs–(Pt electrode) system. The reaction was found to be catalytic (0.25 faraday/mol) and dependent on the electroreduction of formaldehyde and/or nitroalkylbenzene. A variety of nitroalkylbenzenes were transformed to their corresponding mono- and/or bishydroxymethylated derivatives in good yield. The product yield and selectivity were shown to depend on the order of reagent addition, solvent, supporting electrolyte, and structure of the starting nitroalkylbenzenes. A plausible mechanism of the generation of base catalysts (EG base) in electroreductive media is discussed.

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Electrogenerated Base (EG Base) Induced Hydroxymethylation of the Side Chain of Nitroalkylbenzenes with Paraformaldehyde

Abstract

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