31658-22-7Relevant articles and documents
REACTIVITY OF ORGANOTIN COMPOUNDS. XXIII. REACTION OF LEAD TETRAACETATE WITH TRIETHYLSTANNYL AND TRIMETHYLSILYL ETHERS OF THE ENOLS OF CYCLIC KETONES AS A METHOD FOR THE PRODUCTION OF 2-ACETOXY KETONES
Kashin, A. N.,Tul'chinskii, M. L.,Bumagin, N. A.,Beletskaya, I. P.,Reutov, O. A.
, p. 1390 - 1395 (2007/10/02)
The reactions of 1-cyclohexenyloxytriethyltin with lead tetraacetate and (diacetoxyiodo)benzene and the reaction of the trimethylsilyl ethers of the enols of cyclopentanone, cyclohexanone, 2-methylcyclohexanone (2-methyl-1-cyclohexenyloxytrimethylsilane and 6-methyl-1-cyclohexenyloxytrimethylsilane), cholestan-3-one, dl-camphor, and 1-methone with lead tetraacetate at room temperature in methylene chloride were investigated.The reaction of 1-cyclohexenyloxytriethyltin with lead tetraacetate and (diacetoxyiodo)benzene leads to the formation of 2-acetoxycyclohexanone and 2,2'-dioxo-1,1'-bicyclohexyl. 1-Cyclohexenyloxytrimethylsilane reacts with lead tetraacetate, giving (1,2-diacetoxycyclohexyloxy)trimethylsilane and (2-acetoxy-1-cyclo-hexenyloxy)trimethylsilane.As a result of the reactions of the trimethylsilyl ethers of the ketone enols with lead tetraacetate after treatment with BF3Et2O the corresponding 2-acetoxy ketones are obtained.The reaction mechanisms are discussed.
