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

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

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2011, Volume: 60, Number: 11, Pages: 2429-2431 Pages count : 3 DOI: 10.1007/s11172-011-0374-6

Authors

Klenov M.S. ¹ , Churakov A.M. ¹ , Strelenko Yu.A. ¹ , Tartakovsky V.A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

A reaction of N-nitro-O-(4-nitrophenyl)hydroxylamine with nitriles RCN (R = Me, Et, Ph) in the presence of P4O10 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 [NO2C6H4O-N=N=O]+, which eliminates an N2O molecule to form the aryloxenium ion [NO2C6H4O]+. The latter reacts with nitriles RCN at the ortho-carbon atom of the phenyl ring giving 2-R-5-nitro-1,3-benzoxazoles.

Klenov M.S. , Churakov A.M. , Strelenko Y.A. , Tartakovsky V.A.
Reaction of N-nitro-O-(4-nitrophenyl)hydroxylamine with phosphorus pentoxide in the presence of nitriles. New method for the generation of aryloxenium ion
Russian Chemical Bulletin. 2011. V.60. N11. P.2429-2431. DOI: 10.1007/s11172-011-0374-6 WOS Scopus OpenAlex

≡ Web of science:	WOS:000307517100044
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