Bismuth-catalyzed methylation and alkylation of quinone derivatives with tert-butyl peroxybenzoate as an oxidant was written by Yang, Jian;Dong, Yu;He, Shuai;Shi, Zhi-Chuan;Wang, Yu;Wang, Ji-Yu. And the article was included in Tetrahedron in 2019.Formula: C9H10O4 This article mentions the following:
A bismuth-catalyzed methylation of quinones I (R = Me, Bn, H, etc.; R1 = H, Me; R2 = H, Me, Br; R3 = H, Me, Br; R4 = H, Me; R5 = H), II (R = Me; R5 = H; R6 = R7 = Me, OMe) in the presence of tert-Bu peroxybenzoate (TBPB) was developed via a radical reaction mechanism. Particularly, TBPB was used not only as an efficient oxidant, but also as a green Me source in such transformation. Moreover, this method could also be efficiently extended to the alkylation of quinones I (R = Me, Br, OH; R1 = R2 = R3 = R4 = R5 = H), II. This reaction tolerated a series of functional groups and prepared a series of vitamin K3 derivatives I (R5 = cyclopentyl, cyclohexyl, cyclooctyl, hexan-2-yl, hexan-3-yl) and benzoquinones II (R5 = cyclohexyl). Notably, antimalarial parvaquone I (R = OH; R1 = R2 = R3 = R4 = H; R5 = cyclohexyl) was synthesized by the reaction. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Formula: C9H10O4).
2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Formula: C9H10O4
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem