Nitration of 3-Methylaceperidazines with a Large Excess of Fuming Nitric Acid


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Abstract

Nitration of N-acetyl-3-methylaceperidazine with a 2–3-fold excess of nitric acid (d 1.36, 1.48) in glacial acetic acid results in the exclusive formation of mono- and dinitroderivatives. The nitration of 3-methylaceperidazine and its N-alkyl- and N-acetyl-substituted derivatives with a 6–9-fold excess of fuming nitric acid (d 1.54) in the same conditions results in the formation of both the expected products of mono- and dinitration and a product of the electrophilic addition of nitric acid to a double bond of acenaphthene scaffold of the molecule of nitration product.

About the authors

N. I. Omelichkin

Research Institute of Physical and Organic Chemistry

Author for correspondence.
Email: niomelichkin@sfedu.ru
Russian Federation, pr. Stachki 194/2, Rostov-on-Don, 344090

L. G. Minyaeva

Research Institute of Physical and Organic Chemistry

Email: niomelichkin@sfedu.ru
Russian Federation, pr. Stachki 194/2, Rostov-on-Don, 344090

A. A. Milov

Southern Scientific Center of the Russian Academy of Sciences

Email: niomelichkin@sfedu.ru
Russian Federation, Rostov-on-Don, 344006

L. G. Kuz’mina

Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

Email: niomelichkin@sfedu.ru
Russian Federation, Moscow, 119991

V. V. Mezheritskii

Research Institute of Physical and Organic Chemistry

Email: niomelichkin@sfedu.ru
Russian Federation, pr. Stachki 194/2, Rostov-on-Don, 344090

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