Regioselective alkylation of substituted quinones by trialkylboranes

Authors
Bieber, LW Neto, PJR Generino, RM
Citation
Lw. Bieber et al., Regioselective alkylation of substituted quinones by trialkylboranes, TETRAHEDR L, 40(24), 1999, pp. 4473-4476
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
24
Year of publication
1999
Pages
4473 - 4476
Database
ISI
SICI code
0040-4039(19990611)40:24<4473:RAOSQB>2.0.ZU;2-N
Abstract
2-Methoxy-1,4-benzoquinone can be alkylated selectively with trialkylborane s in position 5, giving high yields of 5-alkyl-2-methoxy-1,4-benzoquinones after oxidative work up. In the case of 2-hydroxy-1,4-naphthoquinone, the s ame procedure leads to 3-alkylated products. A radical chain mechanism is p roposed to explain the observed selectivity. (C) 1999 Elsevier Science Ltd. All rights reserved.