36386-49-9Relevant articles and documents
Synthesis and kinetic regularities of the thermal decomposition of new hydrotrioxides of cyclic alcohols
Grabovskiy,Khalitova,Fedorova,Lobov,Rol’nik,Kabal’nova
, p. 464 - 468 (2016)
Cyclic hydrotrioxides were synthesized by low-temperature (?78 °C) ozonolysis of a series of cyclic alcohols and identified using 1H NMR spectra. The kinetic regularities of the thermal decomposition of the synthesized hydrotrioxides were studied. The experimental proof of the induced decomposition of alcohol hydrotrioxides was obtained for the first time using cyclohexanol hydrotrioxide as an example. The influence of cyclic substituents on the thermal stability of the hydrotrioxides is shown.
Chiral β- and γ-aminoalcohols derived from (+)-camphor and (-)-fenchone as catalysts for the enantioselective addition of diethylzinc to benzaldehyde
Dimitrov, Vladimir,Dobrikov, Georgi,Genov, Miroslav
, p. 1323 - 1329 (2007/10/03)
The addition of Me3SiCN and LiCH2CN to (+)-camphor and (-)-fenchone, respectively, followed by reduction leads to chiral β- and γ-aminoalcohols. The enantioselectivities realized using these aminoalcohols as ligands in the addition of Et2Zn to benzaldehyde were lower than those obtained using the corresponding δ-aminoalcohols.
Acid-Catalyzed Rearrangements of the Pinyl System
Muneyuki, Ryonosuke,Yoshimura, Yohko,Tori, Kazuo,Terui, Yoshihiro,Shoolery, James N.
, p. 358 - 366 (2007/10/02)
The additions and rearrangements of α-pinene (1) and apopinene (2) in deuteriated acids have been studied.The results obtained for 1 suggest that one of the reaction paths involves the tertiary cation intermediate 3a, but it has been difficult to define clearly the stereoelectronic relation between additions and rearangements in this system.However, in the case of deuterium addition to 2, the stereospecific deuterium location at C-6-endo in the product 7, the considerable preference for sterically hindered exo-side addition, and the rate enhancement of 48 times for CF3COOH addition to 2 compared with cyclohexane are interpreted to mean that the additions are assisted by concerted C-6-C-1 or C-7-C-1 bond migration corresponding to endo- and exo-side addition, respectively.Furthermore in β-fenchoisocamphorol (9) obtained in CF3COOD addition to 2, the fraction of deuterium at C-1 (0.40) exceeds that at C-2-endo (0.36) as shown in the 2H NMR spectrum.The same result is observed in 9 from model compounds 17 and 18.These facts are interpreted as resulting either from an equilibrium between the cation intermediates I and II, in which II is favored due to the secondary α-deuterium isotope effect on I, or from an isotopic perturbation of resonance in a bridged structure, which favors product formation with deuterium at C-1.
