52789-75-0Relevant articles and documents
Formation of δ-Lactones by cyanide catalyzed rearrangement of α-Hydroxy-β-oxoesters
Kieslich, David,Christoffers, Jens
supporting information, p. 953 - 957 (2021/02/06)
δ-Valerolactone derivatives are formed by cyanide-catalyzed ring-transformation of cyclic α-hydroxy-β-oxoesters. This unprecedented reaction defines a new synthetic methodology, and the products are obtained in up to quantitative yields. Several alkyl substitutions as well as different ester residues are tolerated. Furthermore, benzo- and heteroarene-annulated starting materials are converted without problems. As an additional benefit, the starting materials are straightforwardly accessed by cerium-catalyzed aerobic α-hydroxylation of readily available β-oxoesters.
Thermal and photochemical oxidation of 2-acetylcyclopentanone with atmospheric oxygen
Novikov,Shestak
, p. 1099 - 1110 (2013/07/26)
The major products of thermal (acetone, CaCl2 excess, reflux) and photochemical (acetone or CCl4, room temperature) oxidation of 2-acetylcyclopentanone with atmospheric oxygen are 2-acetyl-2- hydroxycyclopentanone, 2-acetyl-2-hydroxy
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.