Rearrangement of the intermediate 1,4-biradicals in photocycloaddition of cyclohex-2-enones to alkenes

被引：2

作者：

Constien, R ^{[1
]}

Kisilowski, B ^{[1
]}

Meyer, L ^{[1
]}

Margaretha, P ^{[1
]}

机构：

[1] Univ Hamburg, Inst Organ Chem, D-20146 Hamburg, Germany

来源：

RUSSIAN CHEMICAL BULLETIN | 1999年 / 48卷 / 03期

关键词：

1,4-biradicals; 1,3-biradicals; piperidine pyrrolidine ring contraction; biradical biradical rearrangement;

D O I：

10.1007/BF02496171

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two unusual examples of enine/alkene photocycloaddition involving a rearrangement of the intermediate 1,4-biradical are presented. The first reaction proceeds via the addition of one of the radical centers to a carbonyl C atom and subsequent bond cleavage, i.e., with rearrangement to a 1,3-biradical, while the second reaction involves abstraction of an H atom by one of the radical centers.

引用

页码：510 / 512

页数：3

共 9 条

[1] Exploring the 1,5 cyclization of alkyl propargyl 1,4 biradicals
Agosta, WC
Margaretha, P
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (04) : 179 - 182
[2] Andresen S, 1996, J INFORM REC, V23, P13
[3] Photocycloaddition of 4,4-dimethylcyclohexenone to 1,1-diphenylethylene. Evidence for a triplet exciplex intermediate
Caldwell, RA
Hrncir, DC
Munoz, T
Unett, DJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (36) : 8741 - 8742
[4] Crimmins M.T., 1993, ORG REACT, V44, P297
[5] INFLUENCE OF SUBSTITUENTS ON C(6) OF 4,4-DIMETHYL-2-CYCLOHEXENONE ON PHOTOADDITION VS PHOTOCYCLOADDITION TO 2-METHYLPROPENE
CRUCIANI, G
SEMISCH, C
MARGARETHA, P
[J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1988, 44 (02) : 219 - 225
[6] Photoaddition of ethyl 2,2-dimethyl-5-oxo-5,6-dihydro-2H-pyridine-1-carboxylate to 2,3-dimethylbut-2-ene
Jeandon, C
Constien, R
Sinnwell, V
Margaretha, P
[J]. HELVETICA CHIMICA ACTA, 1998, 81 (02) : 303 - 306
[7] KISILOWSKI B, 1996, J CHEM SOC CHEM COMM, P2065
[8] Scaiano J. C., 1978, Rev. Chem. Intermed, V2, P139
[9] Wilson R. M., 1985, ORG PHOTOCHEM, V7, P339

← 1 →