Face Selection in Additions to the Trigonal C2 Site in Quaternized 5-Azaadamantane Derivatives

…, EM Gonikberg, J Hung, WJ le Noble

Index: Lau, Jacqueline; Gonikberg, Elena M.; Hung, Jui-Te; Le Noble, William J. Journal of the American Chemical Society, 1995 , vol. 117, # 46 p. 11421 - 11425

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Citation Number: 22

Abstract

Abstract: The quaternary N-allyl bromide salt 5 of allyl~-[2-(5-azaadamantylidene)] benzyl ether upon warming gave the Claisen rearrangement products 6 is the ratio EIZ= 93: 7. The epoxidation of the N-oxide 8 of 2-methylene-5-azaadamantane 7 with m-CPBA gives rise to the two diastereomeric epoxides 9 in the ratio E1Z= 19: 81. Reaction of the methyl iodide salt of this olefin with bromine in water produces the E-and Z-dibromides 10 in the ratio 74: ...