PHOTOCHEMICAL-REACTION OF ARENECARBONITRILES IN THE PRESENCE OF ALKYLSILANES, SILYL ETHERS AND SILYL AMINES

被引：34

作者：

MELLA, M ^{[1
]}

DALESSANDRO, N ^{[1
]}

FRECCERO, M ^{[1
]}

ALBINI, A ^{[1
]}

机构：

[1] UNIV TURIN, INST ORGAN CHEM, I-10125 TURIN, ITALY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1993年 / 03期

关键词：

D O I：

10.1039/p29930000515

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The irradiation of benzene-1,2,4,5-tetracarbonitrile, and benzene-1,2,4- as well as benzene-1,3,5-tricarbonitrile in the presence of various tetraalkylsilanes, alkoxytrialkylsilanes, hexamethyldisiloxane or heptamethyldisilazane leads to alkylation of the aromatics. The more substituted alkyl group is selectively fragmented, and the attack takes place at the position(s) of highest spin density in the nitrile radical anion. The reaction involves electron transfer to the nitrile's singlet excited state, and the radical cation appears to cleave mainly in the initial radical ion pair.

引用

页码：515 / 519

页数：5

共 30 条

[11]

HESS GG, 1965, J AM CHEM SOC, V87, P5237

[12]

KNIBBE H, 1968, BERICH BUNSEN GESELL, V72, P257

[13] ELECTRON-TRANSFER AND CHARGE-TRANSFER - TWIN THEMES IN UNIFYING THE MECHANISMS OF ORGANIC AND ORGANOMETALLIC REACTIONS [J].