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Photoinduced β‐elimination of the triazole group in the 1‐( N,N ‐bisacyl)amino‐1,2,3‐triazoles
Author(s) -
Kalambokis E. A.,
Maroulis A. J.,
Alexandrou N. E.
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300521
Subject(s) - chemistry , homolysis , hydrogen atom abstraction , bond cleavage , cleavage (geology) , photochemistry , chlorine atom , triazole , intermolecular force , chlorine , electron transfer , medicinal chemistry , hydrogen , radical , molecule , organic chemistry , catalysis , fracture (geology) , engineering , geotechnical engineering
Abstract The photoelimination of the 1,2,3‐triazole group from the title compounds proceeds, depending upon the reaction conditions, via an intra‐ or intermolecular hydrogen abstraction or electron‐transfer mechanism, followed by homolytic cleavage of the N,N bond. It can also proceed via π − ‐assisted β‐cleavage of the same weak bond, when light of shorter wavelength is used. The composition of the products suggests that in all cases most probably a α‐type 1,2,3‐triazolyl radical 10 is eliminated which is further quenched by hydrogen or chlorine abstraction.