Reaction of N-nitro-O-(4-nitrophenyl) hydroxylamine with phosphorus pentoxide in the presence of nitriles. New method for the generation of aryloxenium ion

…, AM Churakov, YA Strelenko, VA Tartakovsky

Index: Klenov, M. S.; Churakov, A. M.; Strelenko, Yu. A.; Tartakovsky, V. A. Russian Chemical Bulletin, 2011 , vol. 60, # 11 p. 2429 - 2431,3

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Abstract

Abstract A reaction of N-nitro-O-(4-nitrophenyl) hydroxylamine with nitriles RCN (R= Me, Et, Ph) in the presence of P 4 O 10 in excess amount at 0° C leads to the formation of 2-R-5- nitro-1, 3-benzoxazoles. The reaction presumably takes place through the intermediate (phenoxy) oxodiazonium ion [NO 2 C 6 H 4 ON= N= O]+, which eliminates an N 2 O molecule to form the aryloxenium ion [NO 2 C 6 H 4 O]+. The latter reacts with nitriles RCN ...

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