Tetrahedron p. 5771 - 5778 (1985)
Update date:2022-08-28
Topics:
Uemura, Motokazu
Take, Kazuhiko
Isobe, Kazuo
Minami, Tatsuya
Hayashi, Yuji
(3-Methoxybenzylalcohol)chromium tricarbonyl (10) and (7-methoxy-1-tetralol)chromium tricarbonyl (12) are selectively lithiated at the 4- and 6-positions, respectively, by treatment with n-BuLi-TMEDA. Since the directed lithiation of the corresponding chromium free arenes normally proceeds at the 2-and 8-positions, complementarily substituted arenes can be prepared by using the chromium tricarbonyl complexes. The difierent position of lithiation is explained by the relative configuration of the chromium tricarbonyl group in the (arene)Cr(CO)3 and electrostatic factors. Some anthraquinones, 31,36,42, and 7-hydroxycalamenenes, 43, have been synthesized through the stereo- and regioselective introduction of substituents by means of(η6-arene)chromium tricarbonyl complexes.
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