82214-84-4Relevant articles and documents
Allylation of quinones with allyl (trifluoro)silanes: Direct synthesis of isoprenoid quinones
Hagiwara, Emiko
, p. 2773 - 2776 (2007/10/02)
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 synthesize biologically active isoprenoid quinones such as plastoquinone-1 and vitamin K1.
Allylation of quinones bu allylic indium reagents
Araki, Shuki,Katsumura, Nobuhito,Butsugan, Yasuo
, p. 7 - 24 (2007/10/02)
Allylation of a variety of quinones by allylic indium sesquihalides was studied.Reactions of unsubstituted p-benzoquinone with allylindium, prenylindium, and geranylindium reagents gave, after oxidation with silver oxide, the corresponding allylated quinones in good yields.These reactions appear to proceed via 1,2-addition of the allylic indium reagents at the γ-carbon followed by sigmatropic rearrangement.Substituted quinones reacted with allylindium reagent giving excellent yields of allylquinols, whereas with prenylindium and geranylindium reagents, trisubstituted quinones gave diprenylcyclohexene-1,4-diones and 2,3-disubstituted quinones gave mixtures of prnylhydroquinones and diprenylcyclohexene-1,4-diones.In the prenylation of haloquinones, 1,2-addition, sigmatropic rearrangement, and elimination of indium(III) halide occurred in sequence yielding prenylquinones. 2-Hydroxy- and 2-methoxy-1,4-naphthoquinones gave α-addition products with prenylindium and cinnamylindium reagents.
