17328-78-8Relevant articles and documents
Structural information from OH stretching frequencies-IX. The influence of γ-alkyl substituents on the different OH rotamers in saturated axial cyclohexanols
Lutz, E. T. G.,Maas, J. H. van der
, p. 743 - 750 (1982)
The sensitivity of the OH-vibration in saturated axial cyclohexanols for γ-alkyl substituents has been studied.It appears that axial γ-substituents considerably influence both, the frequency and the presence of the rotamers.Besides the OH-vibration proves to be sensitive to the type of α-alkyl substituent.At least two types of intramolecular interaction affect the OH-frequency: (i) repulsive lone pair ... β- and γ-alkyl interaction and (ii) β-methyl ... axial β-H interaction.
Electroorganic Chemistry. 140. Electroreductively Intra- and Intermolecular Couplings of Ketones with Nitriles
Shono, Tatsuya,Kise, Naoki,Fujimoto, Taku,Tominaga, Naoto,Morita, Hiroshi
, p. 7175 - 7187 (2007/10/02)
Electroreduction of γ- and δ-cyano ketones in i-PrOH with Sn cathode gave α-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products.Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of γ- and δ-cyano ketones in one of the key steps.Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product.The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.
ORGANOMETALLIC REACTION MECHANISMS. XVIII. CONCERNING THE NATURE OF THE TRANSITION STATE IN THE REACTION OF TRIALKYLALUMINUM COMPOUNDS WITH KETONES
Ashby, E. C.,Smith, R. Scott
, p. 71 - 85 (2007/10/02)
Et2AlCH2AlEt2 (1) has been used as a mechanistic probe to determine the nature of the transition state in the reaction of two equivalents of a trialkylaluminum compound with a ketone in hydrocarbon solvent. 1 was prepared in benzene and the solution composition determined.Low temperature 1H NMR data of 1 as the mono(diethyl etherate) indicate that the ether oxygen is simultaneously coordinated to both aluminum atoms.The reactions of 1 with 4-t-butylcyclohexanone in hydrocarbon solvent were compared to the reactions of triethylaluminium with the same ketone.The results support the importance of a bridging alkyl group described by the formation of a six-centered transition state when two equivalents of a trialkylaluminum compound are allowed to react with a ketone in hydrocarbon solvent.The results also argue against a transition state described by two moles of trialkylaluminum compound complexed to the carbonyl oxygen atom.