Photorearrangement of the ortho-cycloadduct of 6-chloro-1,3-dimethyluracil to benzene through [π4s+π2a] photocycloaddition

被引：0

作者：

Ohkura, K ^{[1
]}

Noguchi, Y ^{[1
]}

Seki, K ^{[1
]}

机构：

[1] Hlth Sci Univ Hokkaido, Fac Pharmaceut Sci, Ishikari, Hokkaido 06102, Japan

来源：

HETEROCYCLES | 1997年 / 46卷

关键词：

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction pathway for the formation of the hydrogen chloride adducts of pyrimidosemibullvalene-2,4-dione derived from the photoreaction of 6-chloro-1,3-dimethyluracil in frozen benzene is interpreted by the mechanism involving the initial ortho-cycloaddition, not meta-cycloaddition, followed by the photochemical disrotatory cleavage of the cyclobutene moiety, and the successive intramolecular photo-Diels-Alder reaction of the resulting cyclooctatetraene ring.

引用

页码：141 / 144

页数：4

共 9 条

[1] Photocycloaddition of 6-chloro-1,3-dimethyluracil to olefins
Ohkura, K
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[2] Acid-catalyzed photocycloaddition of 6-chloro-1,3-dimethyluracil to polycyclic aromatic hydrocarbons
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[J]. HETEROCYCLES, 2003, 59 (02) : 459 - 464
[3] SYNTHESIS OF CYCLOOCTAPYRIMIDINE-2,4-DIONES BY PHOTOCYCLOADDITION OF 6-CHLORO-1,3-DIMETHYLURACIL TO BENZENES IN THE PRESENCE OF TRIFLUOROACETIC-ACID
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[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1993, 41 (02) : 239 - 243
[4] ACID-CATALYZED PHOTOREACTION OF 6-CHLORO-1,3-DIMETHYLURACIL IN BENZENE - SYNTHESIS OF CYCLOOCTAPYRIMIDINE-2,4-DIONE
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[5] MECHANISTIC STUDIES ON THE ANORMALOUS PHOTOCYCLOADDITION REACTION OF 5-STYRYL-1,3-DIMETHYLURACIL AND 2,3-DIMETHYL-2-BUTENE - FORMATION OF THE APPARENT FORBIDDEN (PI-4S+PI-2S) CYCLOADDUCT
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KANG, HK
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[J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1991, 12 (04) : 434 - 437
[6] Acid-catalyzed photoreaction of 6-chloro-1,3-dimethyluracil in frozen benzene: Formation of novel cycloadducts, tetrahydropentaleno[1,2-e]pyrimidine-2,4-dione derivatives
Ohkura, K
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Seki, KI
[J]. CHEMISTRY LETTERS, 1997, (01) : 99 - 100
[7] CYCLO-ADDITIONS IN SYNTHESES .11. PHOTOCYCLOADDITION OF 6-CHLORO-1,3-DIMETHYLURACIL TO ALKENES - SYNTHESIS OF 1,2-DIHYDROCYCLOBUTA[D]PYRIMIDINE-4,6(3H,5H)-DIONES
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SHIMOMURA, N
[J]. TETRAHEDRON LETTERS, 1982, 23 (25) : 2571 - 2574
[8] A NEW RING-SYSTEM FROM PHOTOCYCLOADDITION OF 6-CHLORO-1,3-DIMETHYLURACIL TO P-XYLENE AND M-XYLENE - FORMATION OF 6-METHYLENE-9,11,X-TRIMETHYL-9,11-DIAZAPENTACYCLO[6.4.0.0(1,3).0(2,5).0(4,8)]DODECANE-10,12-DIONES
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[J]. CHEMISTRY LETTERS, 1993, (04) : 667 - 670
[9] Acid-catalyzed photoreaction of 6-chloro-1,3-dimethyluracil to p- and m-xylene: Formation of novel photocycloadducts, 6-methylene-9,11,X-trimethyl-9,11-diazapentacyclo[6.4.0.0(1,3).0(2,5).0(4,8)]dodecane-10,12-diones and 5-methylene-9,11,X-trimethyl-9,11-diazapentacyclo[6.4.0.0(1,3).0(2,6).0(4,8)]dodecane-10,12-diones
Ohkura, K
Seki, K
Hiramatsu, H
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[J]. HETEROCYCLES, 1997, 44 : 467 - 478

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