Reference

Allylation of quinones with allyl(trifluoro)silanes: direct synthesis of isoprenoid quinones

Hagiwara, Emiko; Hatanaka, Yasuo; Gohda, Ken-ichi; Hiyama, Tamejiro (Sagami Chem. Res. Cent., Sagamihara 229, Japan). Tetrahedron Lett., 36(16), 2773-6 (English) 1995. CODEN: TELEAY. ISSN: 0040-4039. 957-78-8 are also occured in this study. DOCUMENT TYPE: Journal CA Section: 25 (Benzene, Its Derivatives, and Condensed Benzenoid Compounds) Section cross-reference(s): 30 Allylation of a variety of quinones with allyl(trifluoro)silanes takes place with high regioselectivity in the presence of FeCl3.6H2O, giving allylquinones in good yields. This method was used to synthesized biol. active isoprenoid quinones such as plastoquinone-1 and vitamin K1. 1,4-Benzoquinone reacted with (3-methyl-2-butenyl)trifluorosilane (I)in presence of Bu4N+F- in THF at -78° to give II. 1,4-Naphthoquinone, FeCl3, H2NCHO were reacted at room temp.for 34 h to give III. To 2,3-dimethyl-1,4-1,4-benzoquinone, I and H2NCHO was added FeCl3 to give plastoquinone-1. .