1195-79-5Relevant articles and documents
Reaction of seleno- or thiofenchone with propiolic acid: Wagner-meerwein rearrangement
Okuma, Kentaro,Matsui, Hiroyuki,Mori, Yuichi
, p. 578 - 583 (2014)
A reaction of selenofenchone with propiolic acid in refluxing chloroform produced 1,3-oxaselenin-6-one, which further reacted with acid to afford the ring-opened product. A reaction of 1,3-oxathiin-6-one prepared from thiofenchone with trifluoroacetic acid gave a Wagner-Meerwein rearranged product. In the presence of AlCl3, thiofenchone reacted with methyl propiolate to afford the corresponding rearranged ester.
Kinetics and mechanisms of the tropospheric reactions of menthol, borneol, fenchol, camphor, and fenchone with hydroxyl radicals (OH) and chlorine atoms (Cl)
Ceacero-Vega, Antonio A.,Ballesteros, Bernabe,Bejan, Iustinian,Barnes, Ian,Jimenez, Elena,Albaladejo, Jose
, p. 4097 - 4107 (2012)
Relative kinetic techniques have been used to measure the rate coefficients for the reactions of oxygenated terpenes (menthol, borneol, fenchol, camphor, and fenchone) and cyclohexanol with hydroxyl radicals (OH) and chlorine atoms (Cl) at 298 ± 2 K and atmospheric pressure. The rate coefficients obtained for the reactions of the title compounds with OH are the following (in units of 10-11 cm3 molecule-1 s-1): (1.48 ± 0.31), (2.65 ± 0.32), (2.49 ± 0.30), (0.38 ± 0.08), (0.39 ± 0.09) for menthol, borneol, fenchol, camphor, and fenchone, respectively. For the corresponding reactions with Cl atoms the rate coefficients are as follows (in units of 10-10 cm3 molecule-1 s-1): (3.21 ± 0.26), (3.40 ± 0.28), (2.72 ± 0.13), (2.93 ± 0.17), (1.59 ± 0.10), and (1.86 ± 0.29) for cyclohexanol, menthol, borneol, fenchol, camphor, and fenchone, respectively. The reported error is twice the standard deviation. Product studies of the reactions were performed using multipass in situ FTIR (Fourier transform infrared spectroscopy) and solid-phase microextraction (SPME) with analysis by GC-MS (gas chromatography-mass spectrometry). A detailed mechanism is proposed to justify the observed reaction products.
Oxidation of Alcohols by Clay-Supported Iron(III) Nitrate; A New Efficient Oxidizing Agent
Cornelis, Andre,Laszlo, Pierre
, p. 849 - 850 (1980)
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Mechanistic and Synthetic Aspects of Intramolecular Alkoxide-Allene Cyclizations
Magnus, Philip,Albaugh-Robertson, Pamela
, p. 804 - 806 (1984)
Intramolecular cyclization of the methoxyallene-alkoxide adducts (1a) proceeds along two different pathways via a methoxyallyl radical anion to give either a dihydrofuran, or vinyl epoxide, depending upon the steric environment of the radical anion.
Palladium(II)-catalyzed ring expansion of a 1-alkenyl cyclopentanol
García Martínez, Antonio,Teso Vilar, Enrique,García Fraile, Amelia,De La Moya Cerero, Santiago,Lora Maroto, Beatriz
, p. 3509 - 3511 (2005)
7,7-Dimethyl-2-methylenenorbornan-1-ol, a strained bicyclic 1-alkenyl cyclopentanol, undergoes Wagner-Meerwein rearrangement to fenchone under treatment with a catalytic amount of PdCl2(PPh3) 2 in refluxing N-methylpyrrolidin-2-one. The described reaction constitutes the first example of the palladium(II)-catalyzed ring expansion of 1-alkenyl cyclopentanols to the corresponding cyclohexanones.