
%0 Journal Article
%A Rossignoli, Monica 
%A Bernhardt, Paul V. 
%A Lawrance, Geoffrey A. 
%A Maeder, Marcel 
%T Macrocycle Formation Through Carbon Acid&#8211;Formaldehyde Condensation Reactions of Bis(propane-1,2-diamine)- and Bis(2-methylpropane-1,2-diamine)-copper(II) Ions
%J Australian Journal of Chemistry
%D 1997/08/19
%V 50
%N 6
%P 529-534
%K 
%R https://doi.org/10.1071/C96219
%U https://www.publish.csiro.au/paper/C96219 
%X The reaction of the bis(1,2-diamine)copper(II) complexes of racemic propane-1,2-diamine (pn) and 2-methylpropane-1,2-diamine (dmen) with formaldehyde and nitroethane in methanol under basic conditions yields minor macrocyclic condensation products in addition to the major acyclic products. Where C-pendant methyl groups on the pair of coordinated diamines are in cis dispositions, the first &#8211;NH&#8211;CH2&#8211;C(CH3)(NO2)&#8211;CH2&#8211;NH&#8211; ring formation occurs at amine pairs distant from these C-methyl substituents, and further reaction to yield a macrocycle is not observed. However, where the C-methyl substituents are in transdispositions, the chemistry proceeds to yield the macrocycle. Commencing with pn, trans-(6,13-diammonio-2,6,9,13-tetramethyl-1,4,7,10-tetraazacyclotetradecane)copper(II) perchlorate formed and crystallized in the space group P 21/n, with a9&#183; 782(2), b 9&#183;2794(6), c 17&#183;017(4) &#197;, &#946; 103&#183;24(1)&#176;. The copper ion is found in a square-planar environment, with the two methyl groups of the pn residues and the pairs of introduced pendant groups all in trans arrangements. 
