PHOTOINDUCED BENZYLATION OF 1,4-DIMETHOXYNAPHTHALENE BY BENZYL HALIDES

被引：2

作者：

ALBINI, A ^{[1
]}

SIVIERO, E ^{[1
]}

MELLA, M ^{[1
]}

LONG, C ^{[1
]}

PRATT, A ^{[1
]}

机构：

[1] DUBLIN CITY UNIV,SCH CHEM SCI,DUBLIN 9,IRELAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1995年 / 10期

关键词：

D O I：

10.1039/p29950001895

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Irradiation of 1,4-dimethoxynaphthalene (DMNH) in the presence of 4-substituted benzyl chlorides (X-C6H4CH2Cl, X = H, Cl, CN or NO2) in either acetonitrile or benzene solution results in benzylation of DMNH, predominantly at position 2 and to a lesser extent on the unsubstituted ring. Steady-state and flash photolysis studies show that charge transfer between singlet excited DMNH and the chlorides is involved. The reaction occurs predominantly in-cage via concerted electron transfer and carbon-chlorine bond cleavage with X = H or Cl, while with X = NO2 fragmentation of the benzyl chloride radical anion occurs out-of-cage, but the process in this case is much less efficient due to competing back electron transfer.

引用

页码：1895 / 1899

页数：5

共 29 条

[1] A NEW METHOD IN RADICAL CHEMISTRY - GENERATION OF RADICALS BY PHOTOINDUCED ELECTRON-TRANSFER AND FRAGMENTATION OF THE RADICAL-CATION [J].