Boratranes with all six-membered rings or with two different ring sizes: Synthesis, characterization, and X-ray crystal structures

Abstract

New types of boratranes B[(O-o-ArCH(2))(3-) (n)N(CH(2)CH(2)O)(n)] (Ar = 2,4-di-MeC(6)H(2); n = 0, 1; n = 1, 2; n = 2, 3) featuring three six-membered chelating ring (1) to two five-membered chelating rings (3) in a stepwise fashion through 2 have been synthesized by the reaction of B(OMe)(3) with a series of tetradentate ligands such as (HO-o-ArCH(2))(3-) (n)N(CH(2)CHOH)(n) (Ar = 2,4-di-MeC(6)H(2); n = 0, L1H(3); n = 1, L2H(3); n = 2, L3H(3)). Compounds 1-3 have been characterized by solution (1)H, (13)C{(1)H} and, (11)B NMR and the crystal structures of 1 and 3 have been determined by single crystal X-ray diffraction. Compounds 1 and 3 are the first structurally characterized boratrane derivatives bearing all six-membered rings and mixed ring systems in the atrane cage, respectively. Especially, the molecular structures of 1 revealed that its transannular N-B bond length of 1.6322(19) angstrom is the shortest among the previously reported boratrane and its derivatives. (C) 2011 Elsevier B.V. All rights reserved.