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Updated: May 30, 2026
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Regioselective O-substitution of C-undecylresorcin[4]arene
Francesco Farina1, Carmen Talotta, Carmine Gaeta
1Dipartimento di Chimica e Biologia, Università di Salerno, Via Ponte don Melillo, I-84084 Fisciano, Salerno, Italy.
Abstract:
Selectively functionalized resorcinarenes were obtained by weak-base-promoted O-alkylation of C-undecylresorcin[4]arene 1. Tetrasubstituted derivatives with C(4)-1,3,5,7, C(2v)-1,2,5,6, C(s)-1,2,4,7, and C(i)-1,2,4,6 pattern were obtained in workable yields by using K(2)CO(3) as the base in acetone at reflux. The good regioselectivity with respect to the statistical distribution was explained in terms of preferential formation of H-bonded monoanions. Heptaaroylated resorcin[4]arenes were also easily obtained by reaction of 1 with aroyl chlorides in pyridine.
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