Alumination of resorcinol and hydroquinone. An easy access to bifunctional Lewis acids
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The reaction of trimethylaluminum with hydrochinone and resorcinol produces [(1,4-(Me2AlO)2C6H4)-THF]2 (1) and [(1,3-(Me2 AlO)2C6H4)-THF]2 (3) respectively. Compounds 1 and 3 are poorly soluble in common solvents but readily dissolve in pyridine to give the corresponding adducts (1,4-(Me2AlO)2C6H4)-(Py)2 (2) and (1,3-(Me2AlO)2C6H4)-(Py)2 (4). The reaction of 4,6-dichlororesorcinol with trimethylaluminum produces the soluble chlorinated analog of compound 3 [1,3-(Me2 AlO)2-4,6-Cl2C6H2)-THF]2 (5). As indicated by NMR, the dimeric structure of 5 is fluxional in solution. Upon addition of chloride or t-butoxide anions to solution of 5 in THF, 27Al NMR monitoring indicates that there is formation of anionic complexes but that the chelation of the anionic hosts by the two aluminum centers present in the [1,3-(Me2AlO)2-4,6-Cl2C6H2] unit does not occur. © 1997 Elsevier Science S.A.
author list (cited authors)
Kaul, F., Tschinkl, M., & Gabbai, F. P.