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翻訳と辞書　辞書検索 [ 開発暫定版 ] スポンサード リンク Vilsmeier–Haack reaction ： ウィキペディア英語版 Vilsmeier–Haack reaction The Vilsmeier–Haack reaction (also called the Vilsmeier reaction) is the chemical reaction of a substituted amide (1) with phosphorus oxychloride and an electron-rich arene (3) to produce an aryl aldehyde or ketone (5). The reaction is named after Anton Vilsmeier and Albrecht Haack.〔Anton Vilsmeier; Haack, A. ''Ber.'' 1927, ''60'', 119.〕〔Meth-Cohn, O.; Stanforth, S. P. ''Comp. Org. Syn.'' 1991, ''2'', 777–794. (Review)〕〔''Formylation of dimethylaniline.'' Campaigne, E.; Archer, W. L. ''Org. Syn.'', Coll. Vol. 4, p.331 (1963); Vol. 33, p.27 (1953). ((Article ))〕 The reaction of a substituted amide with phosphorus oxychloride gives a substituted chloroiminium ion (2), also called the Vilsmeier reagent. The initial product is an iminium ion (4b), which is hydrolyzed to the corresponding aromatic ketone or aldehyde during workup. For example, benzanilide and dimethylaniline react with phosphorus oxychloride to produce an unsymmetrical diaryl ketone.〔''Vilsmeyer-Haack reaction of benzanilide and dimethylaniline.'' Hurd, C. D.; Webb. C. N. ''Org. Syn.'', Coll. Vol. 1, p.217 (1941); Vol. 7, p.24 (1927). ((Article ))〕 Similarly, anthracene can be formylated exclusively at the 9-position.〔''Formylation of anthracene.'' Fieser, F. L.; Hartwell, J. L.; Jones, J. E.; Wood, J. H.; Bost, R. W. ''Org. Syn.'', Coll. Vol. 3, p.98 (1955); Vol. 20, p.11 (1940). ((Article ))〕 The reaction of anthracene with ''N''-methylformanilide, also using phosphorus oxychloride, is shown below: == Reaction mechanism == The reaction of the amide with phosphorus oxychloride produces an electrophilic iminium cation. The subsequent electrophilic aromatic substitution produces an iminium ion intermediate, which is hydrolyzed to give the desired aryl ketone or aryl aldehyde.〔Jones, G.; Stanforth, S. P. ''Org. React.'' 2000, ''56'', 355. 〕 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Vilsmeier–Haack reaction」の詳細全文を読む スポンサード リンク 翻訳と辞書 : 翻訳のためのインターネットリソース Copyright(C) kotoba.ne.jp 1997-2016. All Rights Reserved.