Journal of Organic Chemistry p. 3559 - 3564 (1980)
Update date:2022-09-26
Topics:
Sasaki, Tadashi
Usuki, Arimitsu
Ohno, Masatomi
Catalytic substitution reactions at the adamantane bridgehead were studied by using α,β- and β,γ-unsaturated trimethylsilanes.Treatment of 1-adamantyl (Ad) chloride (1) with allyltrimethylsilane and its heteroanalogues, X=Y-Z-SiMe3, in the presence of Lewis acid as a catalyst gave the products Ad-X-Y=Z, X=Y+(Ad)-Z-, and X=Y-Z-Ad, depending on the attack site of the adamantyl group on each X, Y, and Z atom.Treatment of 1 with (phenylethynyl)trimethylsilane also gave a substituted adamantane in good yield.The substitution reactions of 1 with aryl- and heteroaryltrimethylsilanes under similar conditions occurred at a position distinct from that of acetylation, indicating that adamantylation was not influenced by an electronic effect of the trimethylsilyl group.
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(1980)Doi:10.1016/S0022-328X(00)83049-1
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(2003)Doi:10.1016/S0040-4039(00)78827-7
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(1980)