Specific para-hydroxylation of nitronaphthalenes with cumene hydroperoxidein basic aqueous media

Authors
Zhu, L Zhang, LH
Citation
L. Zhu et Lh. Zhang, Specific para-hydroxylation of nitronaphthalenes with cumene hydroperoxidein basic aqueous media, TETRAHEDR L, 41(19), 2000, pp. 3519-3522
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
19
Year of publication
2000
Pages
3519 - 3522
Database
ISI
SICI code
0040-4039(20000506)41:19<3519:SPONWC>2.0.ZU;2-X
Abstract
A synthetic method for specific para-hydroxylation of nitroarenes has been developed. The reaction of nitronaphthalenes with cumeme hydroperoxide in b asic aqueous media produces exclusively pam-hydroxy nitronaphthalenes in go od yield. The selectivity of ortho and para hydroxylation is mediated by wa ter content. The rationale for water-controlled orientation of hydroxylatio n has been briefly discussed. (C) 2000 Elsevier Science Ltd. All rights res erved.