Miyauchi, Yuta et al. published their research in Chemistry Letters in 2016 | CAS: 16356-02-8

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) 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. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Application of 16356-02-8

Synthesis of functionalized benzobarrelenes and azabenzobarrelenes by rhodium-catalyzed [2+2+2] cycloaddition was written by Miyauchi, Yuta;Shibata, Yu;Tanaka, Ken. And the article was included in Chemistry Letters in 2016.Application of 16356-02-8 This article mentions the following:

It has been established that a cationic rhodium(I)/H8-BINAP complex catalyzes the [2+2+2] cycloaddition of cyclohexadiene- linked 1,7-diynes with monoynes to produce functionalized benzobarrelenes. Functionalized azabenzobarrelenes were also obtained by using BINAP as a ligand and nitriles as coupling partners. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Application of 16356-02-8).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) 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. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Application of 16356-02-8

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem