7714-72-9Relevant academic research and scientific papers
Synthesis of Allylboronates via Zweifel-type Deprotonative Olefination
Xu, Nuo,Xu, Jianeng,Zhu, Qing,Liu, Chao
supporting information, p. 2403 - 2407 (2020/12/30)
A method for the synthesis of allylboronates via Zweifel-type deprotonative olefination was demonstrated. Tetrasubstituted vinylboronates were used as the substrates. NCS (N-chlorosuccinimide) was used as a bifunctional additive, electrophile and base. This method exhibited a different elimination strategy in Zweifel type transformation to afford allylboronates. The homo-alcohols and alkenes were stereoselective synthesized from the obtained allylboronates, demonstrating the synthetic value of this methodology. (Figure presented.).
A method for synthesis of homoallylic bromide
Qi, Wenke,Wang, Peipei,Fan, Liyuan,Zhang, Songlin
, p. 5918 - 5924 (2013/07/26)
Cyclopropyl Grignard reagents react with carbonyl compounds in the presence of diethyl phosphite to give homoallylic bromides. The reaction is effectively carried out under mild conditions in a one-pot fashion with moderate to good yields.
A one-pot cross-pinacol coupling/rearrangement procedure
Scheffler, Ulf,Mahrwald, Rainer
, p. 1970 - 1975,6 (2012/12/12)
A new catalytic retro-pinacol/cross-pinacol reaction, followed by subsequent rearrangement or deoxygenation of the intermediately formed vicinal diols, is described. This operationally simple one-pot protocol allows isolation of geminal α,α-diphenyl ketones or 1,1-diphenyl alkenes with high yields and selectivities. Copyright
NBS-promoted rearrangement of 1,1-diarylmethylenecyclopentane
Chang, Meng-Yang,Lin, Chung-Han
scheme or table, p. 853 - 856 (2012/02/05)
The 1-aroyl-1-aryl-2-bromocyclopentanes 3a, 3b, 3c and 3d (Ar = C 6H5, 2-FC6H4, 3-FC6H 4, 4-FC6H4) were prepared from N-bromosuccinimide (NBS)-promoted rearrangement o
Sp3-sp2 C-C bond formation via Bronsted acid trifluoromethanesulfonic acid-catalyzed direct coupling reaction of alcohols and alkenes
Yue, Hui-Lan,Wei, Wei,Li, Ming-Ming,Yang, Yong-Rong,Ji, Jian-Xin
supporting information; experimental part, p. 3139 - 3145 (2012/01/06)
A novel and efficient trifluoromethanesulfonic acid-catalyzed sp 3-sp2 Ci￡C bond formation reaction through the direct coupling of alcohols with alkenes has been realized under mild conditions. The present protocol provides an attractive approach to a diverse range of polysubstituted olefins in good to excellent yields with high stereo- and regioselectivities. Copyright
Transformation of 1,5- and 1,6-dienes to carbocycles by hydrozirconation and oxidation with cerium(IV) compounds
Azemi, Takushi,Kitamura, Mitsuru,Narasaka, Koichi
, p. 1339 - 1344 (2007/10/03)
Cyclopentane and cyclohexane derivatives are prepared from 1,5- and 1,6-dienes in a one pot procedure by hydrozirconation, then oxidation of the generated 5- and 6-alkenylzirconocene chlorides with ammonium hexanitratocerate.
Adjusting the top end of the alkyl radical kinetic scale. Laser flash photolysis calibrations of fast radical clocks and rate constants for reactions of benzeneselenol
Newcomb,Choi,Horner
, p. 1225 - 1231 (2007/10/03)
Rate constants for 5-exo cyclizations of the 6,6-diphenyl-5-hexenyl radical (1a), the 1-methyl-6,6-diphenyl-5-hexenyl radical (1b), and the 1,1- dimethyl-6,6-diphenyl-5-hexenyl radical (1c) were measured by laser flash photolysis methods, and Arrhenius parameters for these cyclizations were determined. Relative rate constants for cyclizations of radicals 1 and reactions with benzeneselenol were determined by indirect kinetic methods, and the relative Arrhenius parameters for the competing reactions were combined with the parameters for the cyclization reactions to give absolute Arrhenius parameters for the PhSeH reactions. At 20 °C, PhSeH reacts with the 1°, 2°, and 3°radicals 1 with nearly the same rate constants, (1.2 ± 0.1) x 109 M-1 s-1. Absolute Arrhenius parameters for reactions of PhSH and t-BuSH with the primary alkyl radical 1a were calculated using literature values for the competition between cyclization of 1a and reactions with the appropriate thiol and the absolute values for cyclization of 1a determined in this work. The results suggest that rate constants for reactions of primary alkyl radicals with t-BuSH are about 20% smaller than those previously reported. In the case of PhSH, the results are in good agreement with one previously reported set of rate constants but about 35% smaller than another set of rate constants that was subsequently incorporated into fast alkyl radical kinetics. The rate constants for alkyl radical reactions calibrated by competition against reaction with PhSeH and PhSH apparently are 30-40% smaller than those previously reported, and the derived rate constants for the fast radical reactions should be adjusted. An especially noteworthy example is ring opening of the cyclopropylcarbinyl radical, the Arrhenius function for which was determined in part from PhSH trapping results. Using the adjusted rate constants for PhSH and recalculating the Arrhenius parameters for the cyclopropylcarbinyl radical ring opening gives log(k/s- 1) = (13.045 ± 0.10) (6.99 ± 0.09)/θ (kcal/mol, errors at 2σ); the rate constant at 20 °C of 6.7 x 107 s-1 is about 13% smaller than that previously calculated.
Kinetic Studies of the Cyclization of the 6,6-Diphenyl-5-hexenyl Radical. A Test of the Accuracy of Rate Constants for Reactions of Hydrogen Transfer Agents
Ha, Chau,Horner, John H.,Newcomb, Martin,Varick, Thomas R.,Arnold, Bradley R.,Lusztyk, Janusz
, p. 1194 - 1198 (2007/10/02)
Cyclization of the 6,6-diphenyl-5-hexenyl radical (1) to the diphenylcyclopentylcarbinyl radical (2) was studied by indirect and direct methods.Indirect kinetic studies were accomplished by the PTOC-thiol method using hydrogen atom transfer trapping from
Aliphatic diazo compounds. XIV. The synthesis of 7-substituted 3-diazo-2-norbornanones and the infrared and proton and carbon-13 nuclear magnetic resonance spectra of these diazo ketones and their precursors
Yates, Peter,Kronis, John David
, p. 1751 - 1766 (2007/10/02)
syn and anti-7-Isopropyl-2-norbornanone (5 and 6) were prepared by catalitic hydrogenation of 7-isopropylidene-2-norbornanone; syn and anti-7-benzhydryl-2-norbornane (9 and 10) were prepared in analogous fashion.Ketones 5 and 6 and syn- and anti-7-tert-bu
