C-ALKYLATION OF BETA-DIKETONES WITH BENZYLPYRIDINIUM SALTS - EVIDENCE FOR CHAIN RADICAL MECHANISMS

被引：28

作者：

MARQUET, J

MORENOMANAS, M

PACHECO, P

PRAT, M

KATRITZKY, AR

BRYCKI, B

机构：

[1] UNIV AUTONOMA BARCELONA,DEPT CHEM,E-08193 BARCELONA,SPAIN

[2] UNIV FLORIDA,DEPT CHEM,GAINESVILLE,FL 32611

来源：

TETRAHEDRON | 1990年 / 46卷 / 15期

关键词：

D O I：

10.1016/S0040-4020(01)87840-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-(p-Substituted benzyl)-2,4,6-triphenylpyridinium cations react with β -diketone anions by mechanisms which depend on the para-substituent. The p-methoxybenzyl derivative undergoes SN1 displacement yielding O- and C-benzylated products. The pnitrobenzyl compound reacts by a chain radicaloid mechanism and gives high yields of C-pnitrobenzylated diketones. The parent benzyl compound forms some C- and some O-benzylated products, together with bibenzyl, probably by a radical chain reaction which was suppressed by radical traps. © 1990.

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页码：5333 / 5346

页数：14

相关论文

共 31 条

[1] C-ALKYLATION AND N-ACYLATION OF 4-AMINO-1-AZABUTADIENE DERIVATIVES - A CONVENIENT ROUTE TO MONOALKYLATED 1,3-DIKETONES [J].

BARLUENGA, J ;

JARDON, J ;

GOTOR, V .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (06) :802-804

[2]

BOYA M, 1975, TETRAHEDRON LETT, P1727

[3] COBALT MEDIATED REGIOSELECTIVE ALKYLATION OF METHYL 3,5-DIOXOHEXANOATE - PREPARATION OF 5-ALKYL DERIVATIVES OF 4-HYDROXY-6-METHYL-2-PYRONE [J].

CERVELLO, J ;

MARQUET, J ;

MORENOMANAS, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (09) :644-645

[4] ETC - A MECHANISTIC CONCEPT FOR INORGANIC AND ORGANIC-CHEMISTRY [J].

CHANON, M ;

TOBE, ML .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1982, 21 (01) :1-23

[5]

CHEN W, 1984, GAODENG XUEXIAO HUAX, V5, P57

[6] HYDROGEN-BONDING IN ORGANIC-SYNTHESIS .7. INTERMOLECULAR SELF-CONDENSATION OF SOME ENOLIZABLE KETONES IN PRESENCE OF FLUORIDE [J].

CLARK, JH ;

MILLER, JM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (18) :2063-2069

[7] BENZYLIC CHLORIDES IN DARZENS REACTION [J].

DILLING, WL ;

HICKNER, RA ;

FARBER, HA .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (11) :3489-&

[8] ALKYLATION OF BETA-DIKETONES THROUGH THEIR CO(II), CO(III) AND ZN(II) COMPLEXES - 1-BROMOADAMANTANE AS ALKYLATING AGENT [J].

GONZALEZ, A ;

GUELL, F ;

MARQUET, J ;

MORENOMANAS, M .

TETRAHEDRON LETTERS, 1985, 26 (31) :3735-3738

[9] METAL-COMPLEXES IN ORGANIC-SYNTHESIS - PREPARATION OF "ALPHA-(1-ADAMANTYL)-BETA-DICARBONYL COMPOUNDS AND 4-(1-ADAMANTYL)-3,5-DISUBSTITUTED PYRAZOLES AND ISOXAZOLES [J].

GONZALEZ, A ;

MARQUET, J ;

MORENOMANAS, M .

TETRAHEDRON, 1986, 42 (15) :4253-4257

[10] COBALT(II) CHLORIDE BISTRIPHENYLPHOSPHINE CATALYZED ALKYLATIONS OF BETA-DICARBONYL COMPOUNDS [J].

GONZALEZ, A ;

MARQUET, J ;

MORENOMANAS, M .

TETRAHEDRON LETTERS, 1988, 29 (12) :1469-1470

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