Tetrahedron Letters p. 4473 - 4476 (1999)
Update date:2022-07-29
Topics:
Bieber, Lothar W.
Rolim Neto, Pedro J.
Generino, Regina M.
2-Methoxy-1,4-benzoquinone can be alkylated selectively with trialkrylboranes in position 5, giving high yields of 5-alkyl-2-methoxy-1,4- benzoquinones after oxidative work up. In the case of 2-hydroxy- 1,4naphthoquinone, the same procedure leads to 3-alkylated products. A radical chain mechanism is proposed to explain the observed selectivity.
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