SYNTHESIS OF ADAMANTANE COMPOUND HAVING SUBSTITUENT AT ITS BRIDGE HEAD

摘要

PURPOSE:To prepare an adamantane compound substituted selectively and easily with a substituent having complicated structure at the bridge head, easily, in high purity, by reacting a 1-adamantyl halide with a specific trialkylsillyl compound. CONSTITUTION:(A) 1mol of a 1-adamantyl halide (pref. bromide or chloride) is reacted with (B) 1-2mol, pref. 1.1-1.5mol of a compound X=Y-Z-SiR3[X, Y and Z are C, N, O, S or atomic groups containing them; double bond is formed between beta- and tau- atom to Si atom (Y is other than O or S); R is methane or ethane] in the presence of a Lewis acid to introduce the substituent X=Y-Z- to the 1-position of the adamantane. The substituent is, e.g. CH2=CH-CH2-, the group I-III, etc.