A Facile Synthesis of Dibenzylated p-tert-Butylcalix[4]Crowns Under Non- Diluted Reaction Conditions

Hirohito      Tsue; Tatsuya      Takimoto; Rui      Tamura; Chieko      Kikuchi; Shunitz      Tanaka

doi:10.2174/1570178043401117

Abstract

The straightforward synthesis of calix[4]crown derivatives in excellent yields under non-diluted reaction conditions is described. The reactions proceed smoothly at ordinary temperature and substrate concentrations of up to 1 M. Theoretical calculations on the reaction intermediates indicate that preorganization originating from the coordination of oxygen atoms to sodium ions plays an important role in the reaction

Keywords: calix[4]crown, calix[4]arene, cyclization, conformation, reaction mechanism

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Letters in Organic Chemistry

Title: A Facile Synthesis of Dibenzylated p-tert-Butylcalix[4]Crowns Under Non- Diluted Reaction Conditions

Volume: 1 Issue: 3

Author(s): Hirohito Tsue, Tatsuya Takimoto, Rui Tamura, Chieko Kikuchi and Shunitz Tanaka

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Keywords: calix[4]crown, calix[4]arene, cyclization, conformation, reaction mechanism

Abstract: The straightforward synthesis of calix[4]crown derivatives in excellent yields under non-diluted reaction conditions is described. The reactions proceed smoothly at ordinary temperature and substrate concentrations of up to 1 M. Theoretical calculations on the reaction intermediates indicate that preorganization originating from the coordination of oxygen atoms to sodium ions plays an important role in the reaction

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Tsue Hirohito, Takimoto Tatsuya, Tamura Rui, Kikuchi Chieko and Tanaka Shunitz, A Facile Synthesis of Dibenzylated p-tert-Butylcalix[4]Crowns Under Non- Diluted Reaction Conditions, Letters in Organic Chemistry 2004; 1 (3) . https://dx.doi.org/10.2174/1570178043401117