J. Chern, H. Wu
Feb 1, 1997
Citations
0
Influential Citations
8
Citations
Journal
Journal of The Chinese Chemical Society
Abstract
Reactions of 4,6-dimethyl-2β-hydroxy-8-oxo-3,5,7-trioxatetracyclo-[7.2.1.0.4,11.06,10]dodecane 1 with nucleophiles have been studied. Reaction of 1 with alcohols, triethylsilane, allyltrimethylsilane, and methylthiotrimethylsilane in CH2Cl2 in the presence of TiCL4, gave the substitution products 2,7a, 7b, and 7c in 80-90% yields. The substitution reaction took place chemoselectively on the hemiacetal group of I. Reaction of 1 with cyanotrimethylsilane in CH2C12 in the presence of TiCL4, gave compound 8 and the rearranged product 9. The structure of 9 was proven by X-ray analysis.