The photochemical dimerization of 3-heteroaryl-acrylates

被引：16

作者：

D'Auria, M ^{[1
]}

Emanuele, L ^{[1
]}

Esposito, V ^{[1
]}

Racioppi, R ^{[1
]}

机构：

[1] Univ Basilicata, Dipartimento Chim, Via N Sauro 85, I-85100 Potenza, Italy

来源：

ARKIVOC | 2002年

关键词：

3-(2-furyl)acrylates; urocanates; photochemical dimerization;

D O I：

10.3998/ark.5550190.0003.b08

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A detailed explanation of the observed photochemical reactivity of 3-heteroaryl-acrylates is furnished on the basis of a comprehensive review of the photochemical dimerizations of this type of compounds. The reactions occurred in the triplet state of the reagents showing good regio- and stereoselectivities. The regioselectivity can be explained assuming that the dimerization reaction is frontier orbitals controlled. The reaction of the triplet state of a reagent with another molecule of the reagent leads to the formation of the most stable biradical. This behavior induces a control in the relative stereochemistry of the two ester functions. The following cyclization occurs in order to obtain the products under kinetic control. This cyclization allows the formation of the most stable isomers.

引用

页码：65 / 78

页数：14

共 24 条

[1]

AMAROUCHE H, 1984, CR ACAD SCI II, V298, P121

[2]

BOLT J, 1976, TETRAHEDRON LETT, P2595

[3] NONOXIDATIVE DIMERIZATION OF 3,4-DIOXYGENATED CINNAMATES TO ARYLTETRALIN LIGNANS [J].

BOTTA, B ;

IACOMACCI, P ;

VINCIGUERRA, V ;

DELLEMONACHE, G ;

GACSBAITZ, E ;

BOTTA, M ;

MISITI, D .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (12) :3238-3241

[4] TOPOCHEMISTRY .4. CRYSTAL CHEMISTRY OF SOME CIS-CINNAMIC ACIDS [J].

BREGMAN, J ;

SCHMIDT, GMJ ;

OSAKI, K ;

SONNTAG, FI .

JOURNAL OF THE CHEMICAL SOCIETY, 1964, (JUN) :2021-&

[5] TOPOCHEMISTRY .2. PHOTOCHEMISTRY OF TRANS-CINNAMIC ACIDS [J].

COHEN, MD ;

SCHMIDT, GMJ ;

SONNTAG, FI .

JOURNAL OF THE CHEMICAL SOCIETY, 1964, (JUN) :2000-&

[6] PHOTOSENSITIZED REACTIONS OF CINNAMATE ESTERS [J].

CURME, HG ;

NATALE, CC ;

KELLEY, DJ .

JOURNAL OF PHYSICAL CHEMISTRY, 1967, 71 (03) :767-&

[7] Photochemical dimerization of esters of urocanic acid [J].

D'Auria, M ;

Racioppi, R .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1998, 112 (2-3) :145-148

[8]

D'Auria M., UNPUB

[9] Regio- and stereochemical control in the photodimerization of methyl 3-(2-furyl)acrylate [J].

DAuria, M .

HETEROCYCLES, 1996, 43 (05) :959-968

[10] PHOTOCHEMICAL DIMERIZATION OF METHYL 2-FURYLACRYLATE AND 2-THIENYLACRYLATE AND RELATED-COMPOUNDS IN SOLUTION [J].

DAURIA, M ;

PIANCATELLI, G ;

VANTAGGI, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :2999-3002

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