Photochemical deoxygenation of aromatic nitro compounds in triethyl phosphite. Substituent effects and evidence for the involvement aryl nitrenes

RJ Sundberg, BP Das, RH Smith

Index: Sundberg,R.J. et al. Journal of the American Chemical Society, 1969 , vol. 91, p. 658 - 668

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Citation Number: 25

Abstract

Abstract: Nitrobenzene and substituted nitrobenzenes are deoxygenated at 30+ 5" when irradiated in triethyl phosphite solution. Triethyl phosphite is oxidized to triethyl phosphate and the deoxygenated nitro compound is converted to the corresponding triethyl N- arylphosphorimidate and to the aniline derivative. When the nitrobenzene is substituted with an o-alkyl group, rearranged products containing the pyridine ring are also found. ...

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