US EPA

1718172 

Journal Article 

AROMATIC NITRATION UNDER NEUTRAL CONDITIONS USING NITROGEN-DIOXIDE AND OZONE AS THE NITRATING AGENT - APPLICATION TO AROMATIC ACETALS AND ACYLAL 

Suzuki, H; Yonezawa, S; Mori, T 

1995 

Yes 

Bulletin of the Chemical Society of Japan
ISSN: 0009-2673
EISSN: 1348-0634 

68 

6 

1535-1544 

WOS:A1995RJ19400003 

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 isomeric mixture of three nitro compounds, in which the ortho and meta isomers predominate, while aromatic orthoesters are rapidly decomposed to give simply the parent esters. Ring nitration under neutral conditions has been interpreted in terms of a nonclassical mechanism, in which nitrogen trioxide is involved as the initial electrophile.