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Fluorescent Probes from Stable Aromatic Nitrile Oxides
Author(s) -
Minuti Luigi Ferdinando,
Memeo Misal Giuseppe,
Crespi Stefano,
Quadrelli Paolo
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501478
Subject(s) - nitrile , chemistry , cycloaddition , triple bond , fluorescence , benzene , photochemistry , regioselectivity , computational chemistry , bond cleavage , combinatorial chemistry , organic chemistry , double bond , physics , quantum mechanics , catalysis
Stable aromatic nitrile oxides underwent a 1,3‐dipolar cycloaddition reaction with 1‐iodo‐4‐(prop‐2‐yn‐1‐yloxy)benzene to afford the expected isoxazoles in very good yields as single regioisomers. The formation of the 5‐substituted isoxazoles is in agreement with frontier orbital theory. The reductive cleavage of the N–O bond followed by complexation with BF 3 · Et 2 O afforded the corresponding boron complexes, which were further derivatized with a triple bond for click chemistry applications. The photochemical behavior and the fluorescence properties of the derivatives were investigated and discussed, taking theoretical calculations into consideration.