Unusual transformation of 3-alkylfuroxans into 3-(nitrooxyalkyl)furoxans on treatment with a mixture of nitric and sulfuric acids


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Abstract

A versatile one-pot synthesis of 4-substituted 3-(nitrooxyalkyl)furoxans by the reaction of 3-alkylfuroxans with a mixture of nitric and sulfuric acids was developed. A plausible mechanism of this unusual transformation was explained in terms of a new Grob-type fragmentation.

About the authors

V. A. Ogurtsov

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Author for correspondence.
Email: vao@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991

A. V. Shastin

Institute of Problems of Chemical Physics, Russian Academy of Sciences

Email: vao@ioc.ac.ru
Russian Federation, 1 prosp. Akad. Semenova, Chernogolovka, Moscow Region, 142432

S. G. Zlotin

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Email: vao@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991

O. A. Rakitin

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

Email: vao@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991


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