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Regioselective alkylation of substituted quinones by trialkylboranes

✍ Scribed by Lothar W. Bieber; Pedro J. Rolim Neto; Regina M. Generino

Book ID
104261587
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
177 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

2-Methoxy-1,4-benzoquinone can be alkylated selectively with trialkylboranes in position 5, giving high yields of 5-alkyi-2-methoxy-l,4-benzoquinones after oxidative work up. In the case of 2-hydroxy-l,4naphthoquinone, the same procedure leads to 3-alkylated products. A radical chain mechanism is proposed to explain the observed selectivity, o 1999 Elsevier Science Lut. All rights reserved.

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