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Photoreaktionen mit Fulleren‐C 60 [3 + 2]‐Photocycloaddition von 2,3‐Diphenyl‐2 H ‐azirin
Author(s) -
Averdung Johannes,
Albrecht Evelyn,
Lauterwein Jürgen,
Luftmann Heinrich,
Mattay Jochen,
Mohn Holger,
Müller Wolfgang H.,
Meer HansUlrich Ter
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941270431
Subject(s) - chemistry , azirine , cycloaddition , nitrile , ylide , irradiation , adduct , fullerene , photochemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis , ring (chemistry) , physics , nuclear physics
Photoreactions with C 60 ‐Fullerene. [3 + 2] Photocycloaddition of 2,3‐Diphenyl‐2 H ‐azirine Upon irradiation 2,3‐Diphenyl‐2 H ‐azirine ( 2 ) is added to C 60 1 with formation of mono and oligo adducts. 1,9‐(3,4‐Dihydro‐2,5‐diphenyl‐2 H ‐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).