Hypophosphorous acid-iodine: a novel reducing system. Part 1: Reduction of diaryl ketones to diaryl methylene derivatives

被引：57

作者：

Hicks, LD ^{[1
]}

Han, JK ^{[1
]}

Fry, AJ ^{[1
]}

机构：

[1] Wesleyan Univ, Dept Chem, Middletown, CT 06459 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 41期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(00)01359-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mixture of hypophosphorous acid (H3PO2) and iodine in hot acetic acid reduces diaryl ketones quickly and aryl alkyl ketones slowly to the corresponding methylene derivatives. The active reducing agent is hydrogen iodide, generated by reaction between iodine and hypophosphorous acid. (C) 2000 Elsevier Science Ltd. All rights reserved.

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收藏

页码：7817 / 7820

页数：4

相关论文

共 18 条

[1] HYPOPHOSPHOROUS ACID AND ITS SALTS - NEW REAGENTS FOR RADICAL CHAIN DEOXYGENATION, DEHALOGENATION AND DEAMINATION [J].

BARTON, DHR ;

JANG, DO ;

JASZBERENYI, JC .

TETRAHEDRON LETTERS, 1992, 33 (39) :5709-5712

[2] STABILIZATION OF CARBANIONS BY POLARIZATION OF ALKYL-GROUPS ON NON-ADJACENT ATOMS [J].

BORDWELL, FG ;

DRUCKER, GE ;

MCCOLLUM, GJ .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (13) :2504-2510

[3]

GORDON P, UNPUB

[4] Hypophosphite mediated carbon-carbon bond formation: a clean approach to radical methodology [J].

Graham, SR ;

Murphy, JA ;

Coates, D .

TETRAHEDRON LETTERS, 1999, 40 (12) :2415-2416

[5] NOVEL AND CONVENIENT SYNTHESIS OF DIBENZ[A,C]ANTHRACENE [J].

HARVEY, RG ;

LEYBA, C ;

KONIECZNY, M ;

FU, PP ;

SUKUMARAN, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (17) :3423-3425

[6] EFFICIENT REDUCTION OF POLYCYCLIC QUINONES, HYDROQUINONES, AND PHENOLS TO POLYCYCLIC AROMATIC-HYDROCARBONS WITH HYDRIODIC ACID [J].

KONIECZNY, M ;

HARVEY, RG .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (26) :4813-4816

[7] IONIC HYDROGENATION OF ETHYLENE BOND AND DOUBLE BOND OF CARBONYL GROUP [J].

KURSANOV, DN ;

PARNES, ZN ;

BASSOVA, GI ;

LOIM, NM ;

ZDANOVIC.VI .

TETRAHEDRON, 1967, 23 (05) :2235-&

[8]

Marie C, 1901, CR HEBD ACAD SCI, V133, P818

[9]

Marie C, 1901, CR HEBD ACAD SCI, V133, P219

[10] Catalytic transfer hydrogenation of unsaturated ketones and imides via ammonium formate [J].

Pande, PP ;

Joshi, GC ;

Mathela, CS .

SYNTHETIC COMMUNICATIONS, 1998, 28 (22) :4193-4200