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Abstract
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The preparation of the title compound 1 via an 8-step synthesis starting with 3-nitrobenz-aldehyde and with a yield of 5.5% is described. 1 is a heteracarbophane with an azo bridge connecting the two benzene rings. In CHCl3 solution 1 is a mixture of the syn- and anti-form and the special steric requirements of this strained cyclic azo compound are also reflected in its UV/Vis spectrum. 1 reacts easily under the influence of acids, heat, or light by an oxidative coupling of both phenyl groups to give 1,10-(2-thiapropano)-5,6-phenan-throline (14). Elimination of sulfur from 1 to give 1,2-diaza[2.2]metacyclophan-1-ene was not successful.

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