Improved Synthesis of Geodken's Macrocycle through the Synthesis of the Dichloride Salt

J. H. Niewahner , Keith A. Walters and Ashley Wagner
Department of Chemistry, Northern Kentucky University, Highland Heights, KY 41099
J. Chem. Educ., 2007, 84 (3), p 477
DOI: 10.1021/ed084p477
Publication Date (Web): March 1, 2007
History, Education, and Documentation

Abstract

The three-step synthesis of Geodken's macrocycle, H2C22H22N4, (5,14-dihydro-6,8,15,17-tetramethyldibenzo[b,i]-[1,4,8,11] tetraazacyclotetradecahexane), in an overall yield of 65% is described. By utilizing the synthesis of the macrocycle's dichloride salt, H2C22H22N4·2HCl, this new synthetic procedure is an improvement over previously reported preparations. The procedure results in higher overall yield and one less step than that previously reported. This modification also demonstrates the effect of solvent on the nature of the product isolated from a reaction.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Inorganic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Coordination Compounds
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  • Received: August 03, 2009

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