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Direct O -alkylation of p-tert -butyldihomooxacalix[4]arene ( 1 ) with N -(bromopropyl)- or N -(bromoethyl)phthalimides and K 2 CO 3 in acetonitrile was conducted under conventional heating (reflux) and using microwave irradiation and ball milling methodologies. The reactions afforded mono- and mainly distal di-substituted derivatives in the cone conformation, in a total of eight compounds. They were isolated by column chromatography, and their conformations and the substitution patterns were established by NMR spectroscopy ( 1 H, 13 C, COSY and NOESY experiments). The X-ray structures of four dihomooxacalix[4]arene phthalimide derivatives ( 2a , 3a , 3b and 5a ) are reported, as well as their photophysical properties. The microwave (MW)-assisted alkylations drastically reduced the reaction times (from days to less than 45 min) and produced higher yields of both 1,3-di-substituted phthalimides ( 3a and 6a) with higher selectivity. Ball milling did not reveal to be a good method for this kind of reaction.

Conventional vs. Microwave- or Mechanically-Assisted Synthesis of Dihomooxacalix[4]arene Phthalimides: NMR, X-ray and Photophysical Analysis