Synthesis of 9-Phenylacridines via Ortho-Lithiation-Cyclization Sequence* was written by Kinens, A.;Kalnins, T.;Suna, E.. And the article was included in Chemistry of Heterocyclic Compounds (New York, NY, United States) in 2015.COA of Formula: C12H17NO2 This article mentions the following:
Herein, we describe a previously unreported formation of acridines from triarylcarbinols under acidic conditions. Thus, treatment of tertiary alcs. with concentrate aqueous HCl in glacial AcOH at 90闁?provided 9-phenylacridines in 91-92% yield. The starting tertiary alcs. were prepared by double addition of ortho-lithiated pivaloyl anilines to benzoyl chloride in 76 and 68% yield, resp. Overall, the two-step ortho-lithiation cyclization sequence constitutes a convenient approach to 9-phenylacridines. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3COA of Formula: C12H17NO2).
N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) 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. 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.COA of Formula: C12H17NO2
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem