Site-selective [2 + 2 + n] cycloadditions for rapid, scalable access to alkynylated polycyclic aromatic hydrocarbons was written by Kiel, Gavin R.;Bergman, Harrison M.;Tilley, T. Don. And the article was included in Chemical Science in 2020.Quality Control of 1,4-Dimethoxy-2-butyne This article mentions the following:
Here, a general and scalable [2 + 2 + n] (n = 1 or 2) cycloaddition strategy to access polycyclic aromatic hydrocarbons (PAHs) that were decorated with synthetically versatile alkynyl groups and its application to seven structurally diverse PAH ring systems (thirteen new alkynylated PAHs in total) was presented. The critical discovery was the site-selectivity of an Ir-catalyzed [2 + 2 + 2] cycloaddition, which preferentially cyclized tethered diyne units with preservation of other (peripheral) alkynyl groups. The potential for generalization of the site-selectivity to other [2 + 2 + n] reactions was demonstrated by identification of a Cp2Zr-mediated [2 + 2 + 1]/metallacycle transfer sequence for synthesis of an alkynylated, selenophene-annulated PAH. The new PAHs were excellent synthons for macrocyclic conjugated nanocarbons. As a proof of concept, four were subjected to alkyne metathesis catalysis to afford large, PAH-containing arylene ethylene macrocycles, which possess a range of cavity sizes reaching well into the nanometer regime. Notably, these high-yielding macrocyclizations establish that synthetically convenient pentynyl groups could be effective for metathesis since the 4-octyne byproduct was sequestered by 5 Å MS. Most importantly, this work was a demonstration of how site-selective reactions could be harnessed to rapidly build up structural complexity in a practical, scalable fashion. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Quality Control of 1,4-Dimethoxy-2-butyne).
1,4-Dimethoxy-2-butyne (cas: 16356-02-8) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. Ethyl ether is an excellent solvent for extractions and for a wide variety of chemical reactions. It is also used as a volatile starting fluid for diesel engines and gasoline engines in cold weather. Dimethyl ether is used as a spray propellant and refrigerant. Methyl t-butyl ether (MTBE) is a gasoline additive that boosts the octane number and reduces the amount of nitrogen-oxide pollutants in the exhaust. The ethers of ethylene glycol are used as solvents and plasticizers.Quality Control of 1,4-Dimethoxy-2-butyne
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem