131567-49-2Relevant academic research and scientific papers
Regioselective Diboron-Mediated Semireduction of Terminal Allenes
Gates, Ashley M.,Santos, Webster L.
, p. 4619 - 4624 (2019/12/11)
A method for the regioselective reduction of the terminal double bond of 1,1-disubstituted allenes has been developed. In the presence of a palladium catalyst, tetrahydroxydiboron and stoichiometric water, allene semireduction proceeds in high yield to afford Z-alkenes selectively.
Construction of All-Carbon Chiral Quaternary Centers through CuI-Catalyzed Enantioselective Reductive Hydroxymethylation of 1,1-Disubstituted Allenes with CO2
Qiu, Jia,Gao, Shen,Li, Chaopeng,Zhang, Lei,Wang, Zheng,Wang, Xiaoming,Ding, Kuiling
, p. 13874 - 13878 (2019/11/11)
A catalytic enantioselective construction of all-carbon chiral quaternary centers through reductive hydroxymethylation of 1,1-disubstituted allenes with CO2 has been developed. In the presence of a copper/Mandyphos catalyst, CO2 is t
Nickel-catalyzed substitution reactions of propargyl halides with organotitanium reagents
Li, Qing-Han,Liao, Jung-Wei,Huang, Yi-Ling,Chiang, Ruei-Tang,Gau, Han-Mou
, p. 7634 - 7642 (2014/12/11)
A simple and mild catalytic coupling reaction of propargyl halides with organotitanium reagents is reported. The reaction of propargyl bromide with organo-titanium reagents mediated by NiCl2(2 mol%) and PCy3(4 mol%) in CH2
Photochemistry of 3-methyl- and 4-methyl-1,2-dihydronaphthalene in the gas phase1
Duguid, Robert J.,Morrison, Harry
, p. 1271 - 1281 (2007/10/02)
The photochemistry of 3-methyl-1,2-dihydronaphthalene (3-MDHN) and 4-methyl-1,2-dihydronaphthalene (4-MDHN) has been studied in the gas phase. Photolysis of 3-MDHN with 254-nm light produces 2-methyl-1,2-dihydronaphthalene (2-MDHN) as the major primary product. Naphthalene is also formed, apparently as a secondary photoproduct from 2-MDHN. Addition of butane to the photolysis mixture quenches the formation of 2-MDHN while producing a new photoproduct, 1-isopropenylbenzocyclobutene (IBCB). This product is also formed when light centered at 300 nm is used for the photolysis. Photolysis of 4-MDHN vapor with 254-nm light gives three products unique to the gas phase: 1-isopropenyl-2-vinylbenzene (IVB), 3-(o-tolyl)-1,2-butadiene (T12B), and 1-methyl-1,2-dihydronaphthalene (1-MDHN). An apparent alkyl shift product, 3-methyl-1,2-dihydronaphthalene (3-MDHN), and naphthalene are also formed, apparently as secondary photolysis products from 1-MDHN. In addition, several photoproducts common to both the solution and gas phase are detected: 2-(o-tolyl)-1,3-butadiene (T13B), 1-methylbenzobicyclo[3.1.0]hex-2-ene (1-MBBH), 1-methyl-1,4-dihydronaphthalene (1-M-1,4-DHN), 1-methyltetralin (1-MT), and 1-methylnaphthalene (1-MN). Again, the presence of butane during the 254-nm photolysis, or the use of longer wavelength light, gives rise to a new photoproduct, 1-methyl-1-vinylbenzocyclobutene (MVBCB). The fluorescence excitation spectrum for 4-MDHN confirms that 254-nm excitation into S2 leads to minimal population of the emissive vibrational levels of S1. Two pathways appear to dominate the photochemistry: retro [4 + 2] cycloaddition to give o-quinodimethane intermediates and sequential hydrogen shifts. These pathways derive from S2 and/or upper vibrational levels of S1 (S1vib) as indicated by the characteristic responses of their ultimate products to the presence of buffer gas. The benzocyclobutenes are unique; they are postulated to arise through a 2 + 2 closure of a vibrationally relaxed precursor o-quinodimethane or via a [1,3] sigmatropic shift in a uniquely populated set of S1vib levels.
