NOVEL REDUCTION OF 2,6-DI-T-BUTYL-P-QUINOLS WITH SODIUM-BOROHYDRIDE

Authors
NISHINAGA A KOJIMA S MASHINO T MARUYAMA K
Citation
A. Nishinaga et al., NOVEL REDUCTION OF 2,6-DI-T-BUTYL-P-QUINOLS WITH SODIUM-BOROHYDRIDE, Chemistry Letters, (5), 1994, pp. 961-964
Citations number
11
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
5
Year of publication
1994
Pages
961 - 964
Database
ISI
SICI code
0366-7022(1994):5<961:NRO2WS>2.0.ZU;2-4
Abstract
Reduction of 2,6-di-t-butyl-p-quinols with NaBH4 results unexpectedly in the regio- and stereoselective formation of the corresponding dihyd ro-p-quinols. The novel reduction occurs via a quinoxyborohydride anio n intermediate, which regulates the stereochemistry of the 4- and 6-po sitions in the products. Aromatization of the products is blocked by t he t-butyl groups.