Mechanistic duality of the side-chain substitution in electrophilic aromatic nitration. Unexpected large difference in deuterium isotope effect k(H)/k(D) between the side-chain nitration and nitrooxylation of deuterated p-xylenes

Authors
Nonoyama, N Iwaya, M Suzuki, H
Citation
N. Nonoyama et al., Mechanistic duality of the side-chain substitution in electrophilic aromatic nitration. Unexpected large difference in deuterium isotope effect k(H)/k(D) between the side-chain nitration and nitrooxylation of deuterated p-xylenes, TETRAHEDR L, 41(2), 2000, pp. 229-233
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
2
Year of publication
2000
Pages
229 - 233
Database
ISI
SICI code
0040-4039(20000108)41:2<229:MDOTSS>2.0.ZU;2-J
Abstract
A large difference in deuterium kinetic isotope effect observed between the side-chain nitration and nitro-oxylation of deuterated p-xylenes, 1,4-(CH3 )(CD3)C6H4 and 1,4-(CD3)(2)C6D4, suggests the operation of different mechan isms for these two types of side-chain substitution. (C) 1999 Elsevier Scie nce Ltd. All rights reserved.