67820-35-3Relevant academic research and scientific papers
Geminal acylation of α-heterosubstituted cyclohexanones and their ketals
Pottie, Ian R.,Crane, Sheldon N.,Gosse, Anna Lee,Miller, David O.,Burnell, D. Burnell
body text, p. 1118 - 1124 (2011/01/09)
Geminal acylation of derivatives of cyclohexanone with Br, Cl, F, and OCH3 in the α position, and of their corresponding dimethyl ketals, could not be accomplished to a significant extent following published procedures. The transformation was a
Photo-cleavage of carbon-carbon bond of α-iodocycloalkanones giving ω,ω-dialkoxyalkanoic ester in alcohol
Ji, Shun-Jun,Horiuchi, C. Akira
, p. 1645 - 1652 (2007/10/03)
The irradiation at λ > 300 nm of α-iodocycloalkanones with a high- pressure mercury lamp in alcohols containing a small amount of water afforded the corresponding ω,ω-dialkoxyalkanoic ester (65-88%) by photochemical cleavage of the C(I)-C=O bond at room temperature. In the case of a commercial fluorescent lamp as the irradiating light source, photochemical ring-opening products were also obtained. The irradiation of 2α-iodo-5α- and 4β-iodo-5β-cholestan-3-ones in methanol gave methyl 2,2-dimethoxy-2,3- seco-5α-cholestan-3-oate and methyl 4,4-dimethoxy-3,4-seco-5β-cholestan-3- oate in 78 and 62% yields, respectively. The photochemical behavior of the cleavage reaction of α-iodocycloalkanones is also discussed on the basis of 2-hydroxycycloalkanone as an intermediate.
A New α-Iodination of Ketones Using Iodine-Ammonium Cerium(IV) Nitrate in Alcohol or Acetic Acid
Horiuchi, C. Akira,Kiji, Shinji
, p. 421 - 426 (2007/10/03)
The direct α-iodination of various ketones using iodine-ammonium cerium(IV) nitrate in acetic acid or alcohol gave the corresponding α-iodo ketones in high yields. The effect of cerium salt on the iodination of ketones, and the iodination of 5α-cholestan-3-one using several methods are also discussed. In the reaction of 3,3,5-trimethylcyclohexanone and unsymmetrical ketones, such as 2-hexanone and 2-heptanone, using methanol, ethanol, 1-propanol, and 2-propanol, the regioselective iodination product was obtained. In the case of bromination, the reaction of ketones with bromine and ammonium cerium(IV) nitrate also yielded the corresponding α-bromo ketones.
Stereochemically defined cyclohexanediols through the regioselective ring-opening of silylated epoxy alcohols
Adam, Waldemar,Prein, Michael,Richter, Markus J.
, p. 1231 - 1234 (2007/10/03)
The nucleophilic ring-opening of the silylated epoxy alcohol 2 leads to highly functionalized building blocks of defined stereochemistry, whereby the regioselectivity may be controlled through the proper choice of the nucleophilic and the reaction conditi
Electrostatic modulation of hydroxyl group ionization in acidic media. Evidence for the competitive operation of intramolecular SN2 reactions
Negri, Joanna T.,Paquette, Leo A.
, p. 8835 - 8841 (2007/10/02)
The acid-catalyzed cyclodehydration of the cis and trans isomers of 2-substituted 1-(3-hydroxypropyl)cyclohexanols results in the formation of spirocyclic tetrahydrofurans. The stereochemical course of these reactions is highly varied, ranging from a domi
STEREOCHEMICAL STUDIES-XXVI CONFORMATIONAL EQUILIBRIA OF KETALS OF 2-SUBSTITUTED CYCLOHEXANONES
Mursakulov, Ismail G.,Guseinov, M. M.,Kasumov, N. K.,Zefirov, Nikolai S.,Samoshin, V. V.,Chalenko, E. G.
, p. 2213 - 2220 (2007/10/02)
The positions of the conformational equilibria in a series of 2-substituted cyclohexanone ketals have been determined by 1H NMR.For the ethylene ketals 6 the equatorial conformer has been found to be enthalpically preferred.The other ketal syst
