Specific features of the reduction of disubstituted amide derivatives of p-tert-butylcalix[4]arene was written by Alekseeva, E. A.;Basok, S. S.;Rakipov, I. M.;Mazepa, A. V.;Gren’, A. I.. And the article was included in Russian Journal of Organic Chemistry in 2013.Formula: C10H21NO4 This article mentions the following:
Regardless of the reducing agent, the reduction at 25°C and at higher temperatures of the amide groups in a large number of p-tert-butylcalix[4]arene derivatives containing amide fragments with different substituents on the nitrogen atoms was accompanied by hydrogenolysis of the C-N bond with formation of the corresponding O-(2-hydroxyethyl)calixarenes and by partial cleavage of the ether bond between the calixarene framework and the substituent to give compounds with a lower degree of substitution. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Formula: C10H21NO4).
1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) 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. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Formula: C10H21NO4
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem