A Convenient Synthesis of 1,5,9-Trithiacyclododecane

5-Diaminocatechol hydrobromide is a purple microcrystalline solid that is stable to air for approximately 3-5 days if kept dry. On deprotonation of the qua-temized amine, solutions of 4,5-diaminocatechol are pale orange and are extremely air-sensitive but react with a variety of salicylaldehyde derivatives to produce catechol-functionalized salphen derivatives. These bifunctional ligands are yellow to orange in color and have been used in the synthesis of a variety of multimetallic complexes 

Ehrlich and M. T. Bogert, J. Org. Chem. 12, 522 (1947). [The checkers recommend using concentrated HNO3 (90 mL) to H2O (10 mL) and the same conditions listed in the synthesis to obtain complete nitration to dinitroveratroL] 

Malinak.D.T.Rosa,andD.Coucouvanis,/norg. Chem.37,1175(1998) (b)S. M.Malinak, Ph.D. thesis, The University of Michigan, 1998. 

Submitted by RICHARD D. ADAMS and JOSEPH L. PERRIN Checked by ANDREA B. MITCHELL and GREGORY J. GRANT  

Polythioether macrocycles or thiacrowns, as they have been called, have attracted attention because of their ability to serve as good ligands for the transition 

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