60014-85-9Relevant academic research and scientific papers
Long-distance electronic coupling in diferrocenyl compounds with cross-conjugated germinal-diethynylethene bridges
Fan, Yang,Li, Hua-Min,Zou, Guo-Dong,Zhang, Xu,Li, Meng,Wu, Jia-Hui,Zhang, Xin,Lu, Hai-Ting
, p. 99 - 105 (2018)
A series of germinal-diethynylethene (gem-DEE) bridged diferrocenyl compounds, including 1,1-[bis(ferrocenylethynyl)methylene]cyclohexane (1), 1,1-[bis(ferrocenylethynyl)methylene]tetrahydro-2H-pyran (2), and 1,1-[bis(ferrocenylethynyl)methylene]tetrahydr
A Convenient Stereoselective Reduction of Gem-Dibromides with a Combination of Dimethyl Phosphite and Potassium Carbonate
Zhao, Yalei,Chen, Tieqiao,Wang, Xiang-Bo,Han, Li-Biao
, p. 1820 - 1827 (2015/12/12)
An efficient and highly stereoselective reduction of a gem-dibromocyclopropane to the corresponding monobromocyclopropane under mild reaction conditions was developed using a combination of dimethyl phosphite and potassium carbonate. This reaction provided a simple and practical way for the synthesis of the valuable monobromocyclopropanes and β-monobromoalkenes.
Palladium(0)-catalyzed cross-coupling of 1,1-diboronates with vinyl bromides and 1,1-dibromoalkenes
Li, Huan,Zhang, Zhikun,Shangguan, Xianghang,Huang, Shan,Chen, Jun,Zhang, Yan,Wang, Jianbo
supporting information, p. 11921 - 11925 (2015/01/09)
Palladium-catalyzed cross-coupling reactions of 1,1-diboronates with vinyl bromides and dibromoalkenes were found to afford 1,4-dienes and allenes, respectively. These reactions utilize the high reactivities of both 1,1-diboronates and allylboron intermediates generated in the initial coupling.
An approach toward the total synthesis of subergorgic acid
Gilbert, John C.,Yin, Jiandong
, p. 5482 - 5490 (2008/12/20)
Ireland-Claisen rearrangement of a substituted alkenyl cyclopentanecarboxylate provided a monocyclic isomer containing the proper stereochemistry for four of the five stereogenic centers in subergorgic acid. Efforts to construct the additional rings in the molecule were thwarted as a result of steric and other factors. The results provide insights regarding the Ireland-Claisen rearrangement in five-membered ring systems. The formation of spiro-compounds from sterically and stereoelectronically demanding systems as reported herein has the potential to serve as a general strategy for the synthesis of such sub-units in both natural and unnatural products.
Ruthenium-catalyzed cycloisomerization of cis-3-en-1-ynes to cyclopentadiene and related derivatives through a 1,5-sigmatropic hydrogen shift of ruthenium vinylidene intermediates
Datta, Swarup,Odedra, Arjan,Liu, Rai-Shung
, p. 11606 - 11607 (2007/10/03)
We report a new ruthenium-catalyzed cycloisomerization of unactivated cis-3-en-1-ynes, which produces substituted cyclopentadiene and related derivatives. The mechanism of this cyclization is proposed to involve a [1,5]-sigmatropic hydrogen shift of ruthenium-vinylidene intermediates on the basis of deuterium-labeling experiments. Copyright
Novel efficient synthesis of dibromoalkenes. A first example of catalytic olefination of aliphatic carbonyl compounds
Korotchenko, Vasily N.,Shastin, Alexey V.,Nenajdenko, Valentine G.,Balenkova, Elizabeth S.
, p. 1906 - 1908 (2007/10/03)
A new simple and efficient one pot transformation of various aliphatic carbonyl compounds to the corresponding dibromoalkenes is described. A wide range of hydrazones of aldehydes and ketones. prepared in situ, were easily converted into dibromoalkenes by treatment with carbon tetrabromide in the presence of CuCl. The reaction proceeds under mild conditions to give the target products in good to high yields.
Synthesis of Mono and gem-Dihalogeno-olefins from Carbonyl Compounds and in situ Generated Lithium Carbenoids
Barluenga, Jose,Fernandez-Simon, Jose L.,Concellon, Jose M.,Yus, Miguel
, p. 691 - 694 (2007/10/02)
The treatment of carbonyl compounds (5) with dihalogenomethane and lithium dicyclohexylamide at -78 deg C leads after acid hydrolysis to the crude alcohols (6), which by silylation with trimethylchlorosilane-hexamethyldisilazane-pyridine affords the crude
Preparation of Allenes from Geminal Dibromo Olefins and Aldehyds
Haessig, Robert,Seebach, Dieter,Siegel, Herbert
, p. 1877 - 1884 (2007/10/02)
The carbonyl carbons of ketones (acetone, cyclohexanone) and aldehydes (propanal, 2,2-dimethylpropanal, acrolein, benzaldehyde, p-methoxybenzaldehyde) are joined through a single carbon atom (originating from carbon tetrabromide) to give trisubstituted al
Photochemistry of Alkyl Halides. 10. Vinyl Halides and Vinylidene Dihalides
Kropp, Paul J.,McNeely, Steven A.,Davis, Robert Drummond
, p. 6907 - 6915 (2007/10/02)
The photobehavior of the acyclic vinyl iodide 2, the 1-iodocycloalkenes 11-14 and 39, the (halomethylene)cycloalkanes 45-48, and the (dihalomethylene)cyclohexanes 62-64 has been studied.Except for the dichloride 64, which exhibited only radical behavior, each of the halides afforded a mixture of ionic and radical products.The two bromides studied, 48 and 63, afforded lower ratios of ionic to radical products than the corresponding iodides 45 and 62.Irradiation of vinyl iodides was found to be a convenient and powerful method for the generation of vinyl cations, including the highly strained 1-cyclohexenyl and 1-cyclopentenyl cations and the unstabilized α-unsubstituted cations 51 and 54.The latter cations underwent rearrangement to the ring-expanded 1-cycloalkenyl cations 28 and 36, respectively.Lowering the temperature of the irradiation of iodides 13, 14, and 45 resulted in an increased ratio of ionic to radical products.However, iodide 47, which underwent principally fragmentation to enyne 61, showed little temperature effect.
