Synthesis of cinnamaldehydes, esters of cinnamic acids and acylals of cinnamaldehydes by oxidation of arylpropenes with 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ)

被引：26

作者：

Iliefski, T ^{[1
]}

Li, SM ^{[1
]}

Lundquist, K ^{[1
]}

机构：

[1] Chalmers Univ Technol, Dept Organ Chem, SE-41296 Gothenburg, Sweden

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 16期

关键词：

D O I：

10.1016/S0040-4039(98)00213-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Arylpropenes and 3-arylpropenes give cinnamaldehydes (yield approximate to 80%) on oxidation with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in the presence of water. The conversion to aldehydes is promoted by electron-donating groups at the aromatic ring. On DDQ oxidation in the presence of methanol, methyl esters of cinnamic acids are the predominant products. DDQ oxidation of 1- or 3-(3,4-dimethoxyphenyl)-1-propene in the presence of acetic acid gives an acylal [the diacetate of(E)-3-(3,4-dimethoxyphenyl)-2-propene-1,l-diol]. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2413 / 2416

页数：4

共 14 条

[1] UBER DIE BENZYLALKOHOLGRUPPEN DES FICHTENLIGNINS [J].

ADLER, E ;

BECKER, HD ;

ISHIHARA, T ;

STAMVIK, A .

HOLZFORSCHUNG, 1966, 20 (01) :3-+

[2] SYNTHESE DES ALPHA-(3,4-DIMETHOXYPHENYL)-GLYCERINS [J].

ADLER, E ;

BJORKQVIST, KJ .

ACTA CHEMICA SCANDINAVICA, 1951, 5 (02) :241-252

[3] LIGHT-INDUCED, IODINE-CATALYZED AEROBIC OXIDATION OF UNSATURATED TERTIARY-AMINES [J].

GANGLOFF, AR ;

JUDGE, TM ;

HELQUIST, P .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3679-3682

[4] LIGHT-INDUCED OXIDATION OF LIGNIN - BEHAVIOR OF STRUCTURAL UNITS CONTAINING A RING-CONJUGATED DOUBLE-BOND [J].

GELLERSTEDT, G ;

PETTERSSON, EL .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1975, 29 (10) :1005-1010

[5] LIGNIN CHROMOPHORES .4. SYNTHESES OF 1,4-DIARYLBUTA-1,3-DIENES [J].

GIERER, J ;

NILVEBRANT, NO ;

OPARA, AE .

JOURNAL OF WOOD CHEMISTRY AND TECHNOLOGY, 1994, 14 (03) :315-337

[6] An efficient and convenient procedure for preparation of 1,1-diacetates from aldehydes catalysed by expansive graphite [J].

Jin, TS ;

Du, GY ;

Zhang, ZH ;

Li, TS .

SYNTHETIC COMMUNICATIONS, 1997, 27 (13) :2261-2266

[7] OXIDATION OF ARYLPROPENES BY 2,3-DICHLORO-5,6-DICYANOQUINONE [J].

KIEFER, EF ;

LUTZ, FE .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (10) :1519-&

[8] ACID DEGRADATION OF LIGNIN .5. DEGRADATION PRODUCTS RELATED TO PHENYLCOUMARAN TYPE OF STRUCTURE [J].

LUNDQUIST, K ;

HEDLUND, K .

ACTA CHEMICA SCANDINAVICA, 1971, 25 (06) :2199-+

[9]

LUTZ FE, 1970, TETRAHEDRON LETT, V11, P4851

[10]

Nakamura Y., 1976, Wood Research, P101

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