PHOTOREACTIONS WITH C60-FULLERENE - [3+2] PHOTOCYCLOADDITION OF 2,3-DIPHENYL-2H-AZIRINE

被引:51
作者
AVERDUNG, J
ALBRECHT, E
LAUTERWEIN, J
LUFTMANN, H
MATTAY, J
MOHN, H
MULLER, WH
TERMEER, HU
机构
[1] UNIV MUNSTER,INST ORGAN CHEM,ORLEANSRING 23,D-48149 MUNSTER,GERMANY
[2] HOECHST AG,D-65926 FRANKFURT,GERMANY
关键词
FULLERENES; AZIRINES; PHOTOCHEMISTRY; 3 + 2] CYCLOADDITIONS; ELECTRON TRANSFER REACTIONS;
D O I
10.1002/cber.19941270431
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Upon irradiation 2,3-Diphenyl-2H-azirine (2) is added to C60 1 with formation of mono and oligo adducts. 1,9-(3,4-Dihy-dro-2,5-diphenyl-2H-pyrrolo)fulleren-60 (3) has been isolated and identified by standard spectroscopic methods. Mechanistic studies revealed two reaction paths leading to 3, i.e. the classic 1,3-dipolar cycloaddition via the nitrile ylide 4 (direct irradiation) or a route via 2-azaallenyl radical cations 5 (sensitization by photoinduced electron transfer).
引用
收藏
页码:787 / 789
页数:3
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