A bis-hypochlorite adduct of a manganese (IV) salen complex having a chiral (2-Bu-t)-cyclohexane-1,2-diamine linkage (2-tBu) is successfully prepared and characterized by various spectroscopic methods. The reactions of 2-Bu-t with various organic substrates show that 2-Bu-t is capable of sulfoxidation, epoxidation, chlorination, and hydrogen abstraction reactions. However, the enantioselectivity of the epoxidation reactions by 2-Bu-t is much lower than that reported for the catalytic reactions by Jacobsen's catalyst. The low enantioselectivity is consistent with a planar conformation of the salen ligand, which is suggested by circular dichroism spectroscopy. This study suggests that 2-Bu-t is not a reactive intermediate of Jacobsen's enantioselective epoxidation catalysis.