Syntheses and Crystal Structures of Calix[4]arene Dithiocarbazate Schiff Bases

Abstract

Abstract: The regioselective syntheses of novel p-tert-butylcalix[4]arenes with functional aldehyde and dithiocarbazate Schiff base groups were carried out. p-tert-Butylcalix[4]arene was alkylated with o-, p-(ω-chloroalkoxy)-benzaldehydes in the system of K₂CO₃/KI/CH₃CN to give calixarene 1,3-dialdehydes. Then the condensation reactions of active calixarene aldehydes with S-methyl and S-benzyldithiocarbazate, calixarene sulfur-containing Schiff bases were efficiently obtained in satisfied yields. The single crystal analysis of the four representative products shows that calixarene aldehydes and Schiff bases exist in cone conformation and there are interesting intermolecular hydrogen-bands and π···π interaction in the crystals.

Key words: Calixarene, Alkylation, S-Alkyldithiocarbazate, Schiff base, Crystal structure

SUN Jing, LIU Dong-mei, WANG Jin-xiang and YAN Chao-guo*. Syntheses and Crystal Structures of Calix[4]arene Dithiocarbazate Schiff Bases[J]. Chemical Research in Chinese Universities, 2010, 26(4): 572-577.

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