ORIENTATION EFFECT OF SIDE-CHAIN SUBSTITUENTS IN AROMATIC-SUBSTITUTION - INDUCED ORTHO NITRATION

Authors
STRAZZOLINI P VERARDO G GORASSINI F GIUMANINI AG
Citation
P. Strazzolini et al., ORIENTATION EFFECT OF SIDE-CHAIN SUBSTITUENTS IN AROMATIC-SUBSTITUTION - INDUCED ORTHO NITRATION, Bulletin of the Chemical Society of Japan, 68(4), 1995, pp. 1155-1161
Citations number
43
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
68
Issue
4
Year of publication
1995
Pages
1155 - 1161
Database
ISI
SICI code
0009-2673(1995)68:4<1155:OEOSSI>2.0.ZU;2-M
Abstract
The presence of a free carboxyl or ester function on the alpha-carbon of toluene induces the nitration of the phenyl ring in the ortho posit ion at or above the statistical value (chaperon effect), when pure HNO 3 is used in CH2Cl2 solution. This is at variance with the results of classical nitration in H2SO4, where p-nitration predominates by far an d m-nitration occurs at a remarkable extent. The new finding is explai ned in terms of precomplex formation.