No abstract

The title compound, C 32 H 28 N 2 , is a chiral bis-imine in which both imine groups display the common E configuration. The naphthyl groups present different orientations with respect to the central core, as reflected in the dihedral angles of 21.4 (2) and 78.83 (14)° between the benzene and naphthyl mean planes, thus the highest possible C 2 local molecular symmetry is not attained. This C 1 mol­ecular conformation allows multiple C—H⋯π inter­molecular contacts involving all aromatic rings, while no π–π inter­actions are available for the stabilization of the crystal structure. The resulting packing structure is based on mol­ecules stacked along [100].

The title compound, C11H20N2O2S, is an enanti­omerically pure heterocycle-substituted thio­urea synthesized under solvent-free conditions. The thio­urea unit adopts a ZZ conformation, with the HN—(C=S)—NH core almost planar and the tetra­hydro­furfuryl groups placed below and above this plane. The whole mol­ecule thus approximates to noncrystallographic C 2 symmetry. Unexpectedly, the C=S group is not involved in inter­molecular hydrogen bonding, as generally observed in homodisubstituted thioureas. Instead, mol­ecules form a one-dimensional network based on weak N—H⋯O(heterocycle) hydrogen bonding, resulting in a zigzag ribbon-like structure around the crystallographic 21 screw axis along [100].

The microwave-assisted Diels-Alder [4+2]-cycloaddition reaction of chiral heterodienes i.e., enantiomerically pure a-oxo imines and a-diimines with fullerene C 60 is reported. The four new adducts were fully characterized (elemental analysis, IR, 1 H and 13 C NMR, MS).