Improved Synthesis of Larger Resorcinarenes

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• 作者：Paolo Della Sala ; Carmine Gaeta ; Wanda Navarra ; Carmen Talotta ; Margherita De Rosa ; Giovanna Brancatelli ; Silvano Geremia ; Francesco Capitelli ; Placido Neri
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：July 1, 2016
• 年：2016
• 卷：81
• 期：13
• 页码：5726-5731
• 全文大小：346K
• 年卷期：0
• ISSN：1520-6904

文摘

The synthesis of the larger resorcin[5 and 6]arene macrocycles [5]^OMe and [6]^OMe has been realized by a Lewis acid-catalyzed condensation of 1,3-dimethoxy-2-methylbenzene with paraformaldehyde in o-dichlorobenzene as the solvent. The methoxy-resorcin[5 and 6]arenes were quantitatively demethylated by treatment with BBr₃ to obtain the corresponding macrocycles with free OH groups. X-ray studies showed that in the solid state both the conformation and the packing of [6]^OMe and [5]^OMe are driven by C–H···O, C–H···π, and π···π interactions.