A highly efficient Pd-catalyzed decarboxylative ortho-arylation of amides with aryl acylperoxides was written by Li, Dengke;Xu, Ning;Zhang, Yicheng;Wang, Lei. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2014.Electric Literature of C12H17NO2 This article mentions the following:
An efficient palladium-catalyzed decarboxylative ortho-arylation of amides with aryl acylperoxides was developed. A variety of anilide derivatives reacted with aryl acyl peroxides to afford the corresponding ortho-arylation products. N-methoxyarylamide reactants led to the formation of phenanthridinone derivatives (i.e., cyclic Weinreb N-(alkoxy)alkanamide analogs). Under optimized conditions the synthesis of the target compounds was achieved using palladium(II) acetate as a catalyst. Starting materials included N-(phenyl)propanamide derivatives, bis(benzoyl)peroxide, N-(methoxy)benzamide derivatives The title compounds thus formed included biaryl-amide derivatives, such as N-[1,1′-biphenyl]-2-yl-2,2-dimethylpropanamide, 1-[[1,1′-biphenyl]-2-yl]-2-pyrrolidinone (cyclic amide analog), and 5-methoxy-6(5H)-phenanthridinone derivatives (Weinreb amide analogs). In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Electric Literature of C12H17NO2).
N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) 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. But ether is more polar than alkenes. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly autoxidize to form hydroperoxides and dialkyl peroxides. If concentrated or heated, these peroxides may explode. To prevent such explosions, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly.Electric Literature of C12H17NO2
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem