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Structural differentiation of isomeric N ‐oxides
Author(s) -
Rondeau Roger E.,
Steppel Richard N.,
Rosenberg Herbert M.,
Knaak Lawrence E.
Publication year - 1973
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.5570100413
Subject(s) - chemistry , isomerization , lanthanide , reagent , benzotriazole , oxide , structural isomer , irradiation , oxygen atom , photochemistry , computational chemistry , stereochemistry , molecule , organic chemistry , ion , catalysis , physics , nuclear physics
The recently reported photochemical isomerization of 1‐(2‐pyridyl)benzotriazole 3‐oxide to the 2‐oxide created a need for a method of distinguishing between the structural isomers. Nmr experiments using Eu(fod) 3 established the position of the oxygen atoms and also yielded convincing evidence regarding attachment of the lanthanide shift reagent to these multi‐functional compounds. Double irradiation experiments were used to resolve the structural problem while shift gradient considerations led to probable sites of coordination.