PHOTOCYCLOADDITIONS OF SOME ALKYL KETONES TO 1,2-DICYANOETHYLENE, MALEIC ANHYDRIDE, AND 1-METHOXY-1-BUTENE

被引：32

作者：

TURRO, NJ

WRIEDE, PA

机构：

[1] Department of Chemistry, Columbia University, New York

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 11期

关键词：

D O I：

10.1021/jo01263a073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photocycloadditions of several alkyl ketones to 1,2-dicyanoethylene, maleic anhydride, and 1-methoxy-1-butene are described. The cycloadditions are stereospecific in the case of the dicyanoethylenes but nonstereospecific in the case of 1-methoxy-1-butene. Photosensitized geometric isomerization of the ethylenes is an important side reaction. A discussion is given of the scope of these photocycloadditions and the factors which control yields and stereospecificity. © 1969, American Chemical Society. All rights reserved.

引用

页码：3562 / &

共 36 条

[1] PHOTOCHEMISTRY OF SYSTEM DIMETHYL MALEATE-DIMETHYL FUMARATE-ACETONE . A NEW MECHANISM FOR OXETANE FORMATION
ALBONE, ES
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (17) : 4663 - &
[2] Arnold D. R., 1968, ADV PHOTOCHEM, V6, P301
[3] ARNOLD DR, 1964, TETRAHEDRON LETT, P1425
[4] PHOTOLYSIS OF 2-METHYLCYCLOHEXANONE
BADCOCK, CC
PERONA, MJ
PRITCHAR.GO
RICKBORN, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (03) : 543 - &
[5] BARLTROP JA, 1968, TETRAHEDRON LETT, P3235
[6] PHOTOCHEMICAL CONVERSION OF FUMARONITRILE AND ACETONE TO OXETANES
BEEREBOOM, JJ
VONWITTE.MS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (04) : 1231 - +
[7] ULTRAVIOLET IRRADIATION OF CARBONYL COMPOUNDS IN CYCLOHEXENE AND 1-HEXENE
BRADSHAW, JS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (01) : 237 - &
[8] CHALPANOVA I, 1954, CA 24358A, V54
[9] DALTON JC, IN PRESS
[10] ON MECHANISM OF PHOTOCHEMICAL DECOMPOSITION OF CYCLOBUTANONE IN GAS PHASE
DENSCHLAG, HO
LEE, EKC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (18) : 4795 - +

← 1 2 3 4 →