Synthesis of phenols and naphthol with n-morpholinomethyl pendants and their dimethylgallium complexes:: crystal structure of dimethylgallium-[4-nitro-2-(n-morpholinomethyl)-1-phenoxide]

The one-pot Mannich reaction was used to synthesize 2-(n-morpholinomethyl)-1-phenol (la), 4-methyl-2-(n-morpholinomethyl)-1-phenol (Ib), 4-chloro-2-(n-morpholinomethyl)-1-phenol (Ic), 4-nitro-2-(n-morpholinomethyl)-1-phenol(ld), and 1-(n-morpholinomethyl)-naphthol (le). The dimethylgallium complexes of these compounds have been prepared, and compound 2d has been determined by X-ray crystallography. The complex 2d crystallized with one unit having two identical molecules which have intermolecular contacts between the two phenyls caused by face to face pi-pi stacking. The Ga-O bond distances are noticeably shorter than in the other dimethylgallium phenoxides reported. (C) 1999 Elsevier Science S.A. All rights reserved.