Rhodium-Catalyzed Cross-Cyclotrimerization and Dimerization of Allenes with Alkynes was written by Sakashita, Kazuki;Shibata, Yu;Tanaka, Ken. And the article was included in Angewandte Chemie, International Edition in 2016.Synthetic Route of C6H10O2 This article mentions the following:
It has been established that a cationic rhodium(I)/binap complex catalyzed the cross-cyclotrimerization of two mols. of a monosubstituted allene with one mol. of a functionalized alkyne gave 3,6-dialkylidenecyclohex-1-enes. In contrast, the reactions involving di- or trisubstituted allenes and/or unfunctionalized alkynes afforded cross-dimerization products, substituted dendralenes, through β-hydrogen elimination from the corresponding rhodacycles. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Synthetic Route of C6H10O2).
1,4-Dimethoxy-2-butyne (cas: 16356-02-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. 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.Synthetic Route of C6H10O2
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem