Determination of solvent-trapped products obtained by photolysis of aryl azides in 2,2,2-trifluoroethanol.
A series of nonfluorinated and fluorinated aryl azides with varied functionality patterns were irradiated in 2,2,2-trifluoroethanol with either a high-pressure or a low-pressure mercury lamp. Interestingly, one of the major products in these reactions was the result of the recombination of anilino and alkyl radicals to form the corresponding hemiaminal compounds. The structure of the recombination products was assigned unambiguously after proton/deuterium exchange experiments followed by MS and MS/MS analysis.
Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8601, Japan.
Magne O
MO
Sydnes
Issei
I
Doi
Ayako
A
Ohishi
Masaki
M
Kuse
Minoru
M
Isobe
D001386:Azides / Q000737:chemistry*; D013058:Mass Spectrometry; D019920:Photoaffinity Labels; D010782:Photolysis; D012997:Solvents / Q000737:chemistry*; D014270:Trifluoroethanol / Q000737:chemistry*
D001386:Azides; D019920:Photoaffinity Labels; D012997:Solvents; D014270:Trifluoroethanol