Organosilicon ethers of oximes

Synthesis of adamantane derivatives. 49. Substitution reaction of 1-adamantyl chloride with some trimethylsilylated unsaturated compounds

“…-Trimethylsilylated oximes showed different behavior from the previously described allyltrimethylsilane heteroanaloues. 0-(Trimethylsilyl)propionaldoxime (31) produced only the O-adamantyl oxime 32 on catalytic action of zinc chloride, but 0-(trimethylsilyl)benzaldoxime (33), in contrast, produced N-adamantylbenzamide (34). Although a mechanism for the formation of the amide was not clarified, the intuitive evidence for attack of the adamantyl group on the central nitrogen atom (eq 2) was obtained under the conditions in which the aluminum chloride catalyzed reaction at low temperature was conducted, giving a nitrone (35) as a product (Scheme II).…”