Aromatic Nitration under Neutral Conditions Using Nitrogen Dioxide and Ozonne as the Nitrating Agent. Application to Aromatic Acetals and Acylal.

H Suzuki, S Yonezawa, T Mori

Index: Suzuki, Hitomi; Yonezawa, Shuji; Mori, Tadashi Bulletin of the Chemical Society of Japan, 1995 , vol. 68, # 6 p. 1535 - 1544

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Citation Number: 17

Abstract

Cyclic acetals derived from aromatic carbonyl compounds can be nitrated smoothly with nitrogen dioxide in ice-cooled dichloromethane or acetonitrile in the presence of ozone and magnesium oxide to give ortho-and para-nitro derivatives as the major product in good combined yields, the acetal ring as a protective group remaining almost intact. An acylal derived from benzaldehyde similarly undergoes nitration on the aromatic ring to give an ...