HALOACYLOXYLATION .3. REACTION OF ALKYL IODIDES WITH PERACETIC ACID IN PRESENCE OF CYCLOHEXENE

被引：23

作者：

OGATA, Y

AOKI, K

机构：

[1] Department of Applied Chemistry, Faculty of Engineering, Nagoya University, Chikusa-ku, Nagoya

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 12期

关键词：

D O I：

10.1021/jo01264a049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of cyclohexyl iodide with peracetic acid in acetic acid at 30° affords l-iodo-2-acetoxycyclohexane (70–80%), together with smaller amounts of cyclohexyl acetate, iodine, and 1,2-diacetoxycyclohexane. Treatment of alkyl iodides with peracetic acid in the presence of cyclohexene in acetic acid also affords 1-iodo-2-acetoxycyclohexane in moderate yields (33–55%). In general, secondary alkyl iodides give yields higher than those from primary alkyl iodides. A mechanism is suggested which involves the reaction of alkyl iodides with peracetic acid to give acetyl hypoiodite, which then adds to the double bond of cyclohexene. © 1969, American Chemical Society. All rights reserved.

引用

页码：3978 / &

共 13 条

[1]

BIRKENBACH L, 1932, BER, V65, P1339

[2]

CLUTTERBUCK PW, 1923, J CHEM SOC, V123, P2511

[3]

COLEMAN GH, 1964, ORGANIC SYNTHESES, V1, P183

[4] REACTIONS OF PER ACIDS .1. THE REACTION OF PERBENZOIC ACID WITH SOME SIMPLE KETONES [J].

FRIESS, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (01) :14-15

[5] STUDIES ON IODINATION OF AROMATIC COMPOUNDS BY MIXTURE OF PEROXYACETIC ACID + IODINE [J].

OGATA, Y ;

NAKAJIMA, K .

TETRAHEDRON, 1964, 20 (12) :2751-&

[6] IODINATION OF AROMATIC COMPOUNDS WITH MIXTURE OF PEROXYACETIC ACID + IODINE [J].

OGATA, Y ;

NAKAJIMA, K .

TETRAHEDRON, 1964, 20 (01) :43-&

[7]

OGATA Y, 1965, CHEM IND-LONDON, P304

[8] IODINATION OF AROMATIC COMPOUNDS WITH A MIXTURE OF IODINE AND PERACETIC ACID .3. AUTOCATALYSIS AND RELATIVE RATES [J].

OGATA, Y ;

AOKI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (22) :6187-&

[9] REACTION OF ALKYL IODIDES WITH PERACETIC ACID IN PRESENCE OF AROMATIC COMPOUNDS [J].

OGATA, Y ;

AOKI, K .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (12) :3974-&

[10] HALOACYLOXYLATION .2. ADDITION OF BROMINE OR CHLORINE TO PROPYLENE IN PRESENCE OF PERACETIC ACID [J].

OGATA, Y ;

AOKI, K .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) :4181-&

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