2-Methyl-benzimidazolium nitrate.

In the title compound, C(8)H(9)N(2) (+)·NO(3) (-), inter-molecular N-H⋯O hydrogen bonds join the mol-ecules into a chain extending along the b axis.

An efficient catalyst system for Pd-catalyzed amination of [2.2]paracyclophanyl bromides.

A practical Buchwald-Hartwig amination of [2.2]paracyclophanyl bromides with benzhydrylideneamine is developed. The method provides a facile route to a variety of imino and amino [2.2]paracyclophanes that are otherwise not readily synthesized.

Design and synthesis of planar chiral heterocyclic carbene precursors derived from [2.2]paracyclophane.

A unique family of planar chiral symmetrical N-heterocyclic carbene precursors with restricted flexibility derived from [2.2]paracyclopane were obtained by a new synthetic route. The resolution of 4-amino-13-bromo[2.2]paracyclophane was achieved with relatively high efficiency. Starting from (4 S p,13 R p)-4-amino-13-bromo[2.2]paracyclophane, the planar chiral pseudogem-disubstituted [2.2]paracyclophanyl dihydroimidazoliums were prepared in a four-step sequence with good yields. The resulting dihydroimidazolium salts were fully characterized with a series of methods including single-crystal X-ray diffraction technique.