SOLUTION PHOTOCHEMISTRY OF SUBSTITUTED CYCLOHEPTATRIENES

被引：16

作者：

BREMBER, AR ^{[1
]}

FREESTONE, VC ^{[1
]}

GORMAN, AA ^{[1
]}

SHERIDAN, JB ^{[1
]}

机构：

[1] UNIV MANCHESTER,DEPT CHEM,MANCHESTER M13 9PL,LANCASHIRE,ENGLAND

来源：

TETRAHEDRON | 1979年 / 35卷 / 19期

关键词：

D O I：

10.1016/0040-4020(79)80126-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The solution photochemistry of several ethoxycarbonyl- and ethoxycarbonyl-methoxy-substituted cycloheptatrienes has been investigated. The results have been used to analyse the directional specificity of ring-closure and 1,7-hydrogen migration reactions. This specificity is interpreted in terms of polarisation within the S1 state which undergoes either (a) allowed photochemical reactions to give the observed products directly or (b) isomerisation to a trans, cis, cis-cyclohepatriene which then reacts via allowed ground-state processes. In at least two instances the directional specificity of the ring-closure reaction is wavelength dependent and this is attributed to the differing reactivities of the S1 and S2 states. © 1979.

引用

页码：2311 / 2322

页数：12

共 36 条

[1] RING INVERSION IN CYCLOHEPTATRIENE [J].

ANET, FAL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (03) :458-&

[2] SYNTHETIC EXPERIMENTS IN THE CYCLOHEPTATRIENONE SERIES .2. 4-KETOCYCLOHEPTATRIENECARBOXYLIC ACID [J].

BARTELSKEITH, JR ;

JOHNSON, AW ;

LANGEMANN, A .

JOURNAL OF THE CHEMICAL SOCIETY, 1952, (NOV) :4461-4466

[3]

BLAIR JA, 1970, CHEM COMMUN, P1319

[4] PHOTOCHEMICAL CONVERSION OF 7-METHOXYCYCLOHEPTATRIENE TO 1-METHOXYBICYCLO[3.2.0]HEPTA-3,6-DIENE [J].

BORDEN, GW ;

CHAPMAN, OL ;

SWINDELL, R ;

TEZUKA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (12) :2979-+

[5]

BORG APT, 1967, CHEM COMMUN, P1210

[6]

BREMBER AR, 1973, TETRAHEDRON LETT, P475

[7]

BREMBER AR, 1970, TETRAHEDRON LETT, P2511

[8]

BREMBER AR, 1971, TETRAHEDRON LETT, P653

[9]

BREMBER AR, UNPUBLISHED

[10] REARRANGEMENT-ADDITION REACTIONS OF BETA,GAMMA-UNSATURATED KETONES IN AQUEOUS ACID [J].

CARGILL, RL ;

POND, DM ;

LEGRAND, SO .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (02) :359-&

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