
TY  - JOUR
A1  - Wei, G 
A1  - Allen, CC 
A1  - Hambley, TW 
A1  - Lawrance, GA 
A1  - Maeder, M 
T1  - Metal-Directed Synthesis of Dithia Diaza Macrocycles Carrying Pendant Alcohol and Also Nitro or Carboxylate Groups
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1995
VL  - 48
IS  - 4
SP  - 825
EP  - 833
KW  - 
UR  - https://doi.org/10.1071/CH9950825 
N2  - Copper(II)-directed condensation of 1,9-diamino-3,7-dithianonan-5-ol with nitroethane or di-ethyl malonate yields (6-methyl-6-nitro-1,11-dithia-4,8-diazacyclotetradecan-13-ol)copper(II) and (diethyl 13-hydroxy-1,11-dithia-4,8-diazacyclotetradecane-6,6-dicarboxylate)copper(II) respectively in good yields, with the latter readily converted by decarboxylation into the complex of ethyl 13-hydroxy-1,11-dithia-4,8-diazacyclotetradecane-6-carboxylate. Analogues without the alcohol group based on 3,7-dithianonane-1,9-diamine are also described. The pendant alcohol group fused directly to a macrocyclic ring carbon can act as an axial donor group, as illustrated in the X-ray crystal structure analysis of (diethyl 13-hydroxy-1,11-dithia-4,8-diazacyclotetradecane-6,6-dicarboxylate)copper(II) perchlorate . This complex crystallizes in the P21/c space group, a 12.650(3), b 8.620(1), c 24.382(4) &#506;, &#946; 96.10(2)&#176;. The copper ion lies in a distorted square-based pyramidal environment of two sulfur donors (average Cu-S 2.338 A), two nitrogen donors (average Cu-N 2.035 &#506;) and the pendant alcohol donor [Cu-O 2.319(6) &#506;], with the copper ion displaced slightly (0.043 &#506;) out of the macrocycle donor plane towards the pendant alcohol donor. 
ER  -

