Reaction of M(tBu)3 with anthranilic, salicylic and ortho-toluic acids yields [(tBu)2M(μ-O2CC6H4-2-NH2)]2, M = Al (1), Ga (2), [(tBu)2Ga(μ-O2CC6H4-2-OH)]2 (3), and [(tBu)2Ga(μ-O2CC6H4-2-Me)]2 (4), respectively. Reaction of anthranilic acid with two equivalents of Al(tBu)3 allows for the isolation of (tBu)2Al(μ-O2CC6H4-2-NH2)Al(tBu)3 (5). Compounds 1–5 have been characterized by NMR and IR spectroscopy, mass spectrometry, and X-ray crystallography. The presence of intra-molecular hydrogen bonding, in compounds 1–3, is probed by the orientation of the aromatic rings. Compound 5 is proposed to be a Lewis acid stabilized complex of the intermediate in the synthesis of compound 1.
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