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107-19-7Relevant articles and documents
The influence of the organolithium reagent nature on the possibility of the O→Csp migration of the R3Si group in propynes HC≡CCH2OSiR3
Novokshonov,Medvedeva,Mareev
, p. 2264 - 2268 (2017)
A possibility of the O→Csp 1,4-migration of the R3Si group in silyl ethers of terminal acetylenic alcohols upon treatment with organolithium reagents (RLi) was studied. In the case of 3-trimethylsilyloxypropyne, depending on the nature of RLi, the heterolysis of the Si—O bond occurs either by the action of acetylide formed as a result of deprotonation with the formation of 3-trimethylsilylprop-2-yn-1-ol trimethylsilyl ether, or by the action of the metalation agent with the formation of propargyl alcohol. The realization of the O→Csp 1,4-migration of the Me3Si group requires the use of mild organolithium reagents (lithium hexamethyldisilazanide and diisopropylamide). Silyl ethers having steric hindrance at the carbon atom bonded to the reaction center or around the silicon atom do not react with the studied organolithium reagents.
Reaktionen eines hydridisch polarisierten Wolframwasserstoff-Komplexes
Kundel, Peter,Berke, Heinz
, p. 353 - 358 (1987)
Reaction of (OC)2ON2WH (1) with acetic acid or phenol, respectively, yields an acetato or a phenolato complex (OC)nON2WX; n = 1, X = CH3COO (2a); n =2, X = PhO (2b). 1 reduces aliphatic, α,β-unsaturated or aromatic aldehydes in the presence of acetic acid or phenol to yield alcohols in most cases.Crotonaldehyde reacts with 1 and phenol to produce butyraldehyde.
Visible Light-Induced Oxygen Transfer from Nitrogen Dioxide to Ethyne and Propyne in a Cryogenic Matrix. 2. Mechanism and Regioselectivity
Harrison, James A.,Frei, Heinz
, p. 12152 - 12157 (1994)
The kinetics of visible ligth-induced oxidation of ethyne and propyne by NO2 in solid Ar has been monitored as a function of photolysis wavelength.CW dye and Ar ion laser emission was used for irradiation, and FT-infrared spectroscopy for the measurement of product growth.Determination of the wavelength dependence of quantum efficiencies from the kinetic measurements revealed that the photolysis threshold of HCCH + NO2 lies approximately 6 kcal mol-1 higher than that of CH3CCH + NO2.This and other parameters derived from the product growth measurements, and the formyl methyl iminoxy radical trapped in the case of the CH3CCH + NO2 reaction are interpreted in terms of a direct O transfer mechanism.The proposed path involves large-amplitude O transfer from photoexcited NO2 to the CC group to yield a transient ketocarbene.Formation of iminoxy radical is attributed to trapping of the ketocarbene by NO cage coproduct, which is in competition with Wolff rearrangement to yield ketene.From the structure of the iminoxy radical, it is inferred that the photoinduced O transfer from NO2 to the unsymmetrical CC bond of propyne is completely regioselective, leading exclusively to the carbene transient with oxygen at the terminal carbon.This regiochemical outcome is interpreted in terms of potential energy profiles for central and terminal carbon attack of the triple bond.
Study of the regioselectivity in the hydrotelluration of hydroxy alkynes
Stefani, Hélio A.,Cardoso, Lincoln D. G.,Valduga, Claudéte J.,Zeni, Gilson
, p. 167 - 172 (2001)
Vinylic tellurides were synthesized by the addition of organotellurols to acetylenic alcohols and the regioselectivity of the reaction was evaluated.
Visible Light-Induced Oxygen Transfer from Nitrogen Dioxide to Ethyne and Propyne in a Cryogenic Matrix. 1. Identification of Products
Harrison, James A.,Frei, Heinz
, p. 12142 - 12151 (1994)
Photochemical reaction of ethyne*NO2 and propyne*NO2 pairs isolated in solid Ar has been observed at wavelengths as long as 582 nm (HCCH*NO2) and 615 nm (CH3CCH*NO2).Continuous wave dye laser radiation was used to excite the reactants, and the chemistry was monitored by FT-infrared spectroscopy.In the case of ethyne + NO2, the sole products were CH2=C=O and NO.The reaction of NO2 with propyne gave methylketene plus a trapped intermediate, CH3C(=NO.)C(=O)H (formyl methyl iminoxy radical).Infrared spectra of this radical are reported for the first time.Product identification was based on D, 18O, and 15N isotopic substitution.Selective interconversion with tuned visible laser light revealed the presence of four conformers, most probably originating from isomerism about the C-C and the C=N bonds.Photoelimination of NO from the iminoxy radical was observed at wavelengths as long as 625 nm.Propynol and methylketene could be identified among the secondary photolysis products.
Ni-catalyzed direct carboxylation of propargylic alcohols with carbon dioxide
Yamahira, Tatsuya,Onodera, Gen,Fukuda, Tsutomu,Kimura, Masanari
supporting information, p. 853 - 855 (2021/05/19)
The carboxylation of propargylic alcohols containing a silyl group at the terminal position was conducted in a CO2 atmosphere at atmospheric pressure in the presence of a nickel catalyst and diethylzinc. Here, CO2 was used as not only the C1 source but also the promoter of the COH cleavage processes for the oxidative addition of propargylic alcohols.
Regiospecific Synthesis of Calcium-Independent Daptomycin Antibiotics using a Chemoenzymatic Method
Mupparapu, Nagaraju,Lin, Yu-Hsin Cindy,Kim, Tae Ho,Elshahawi, Sherif I.
supporting information, p. 4176 - 4182 (2021/02/01)
Daptomycin (DAP) is a calcium (Ca2+)-dependent FDA-approved antibiotic drug for the treatment of Gram-positive infections. It possesses a complex pharmacophore hampering derivatization and/or synthesis of analogues. To mimic the Ca2+-binding effect, we used a chemoenzymatic approach to modify the tryptophan (Trp) residue of DAP and synthesize kinetically characterized and structurally elucidated regiospecific Trp-modified DAP analogues. We demonstrated that the modified DAPs are several times more active than the parent molecule against antibiotic-susceptible and antibiotic-resistant Gram-positive bacteria. Strikingly, and in contrast to the parent molecule, the DAP derivatives do not rely on calcium or any additional elements for activity.
Method for synthesizing propargyl alcohol
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Paragraph 0040-0066, (2021/11/21)
The method comprises the following steps: taking potassium hydroxide or potassium alcoholate as a catalyst, and reacting with acetylene below 0.15 mpa pressure in an aromatic hydrocarbon or aliphatic hydrocarbon organic solvent to form propinyl alcohol. The reaction end point material is a 'liquid - liquid' two-phase system and is separated by sedimentation. The product is recovered by hydrolysis separation, extraction purification and rectification separation, and the yield of propargol in the product can reach 71% - 73%.
Palladium-Catalyzed Selective Reduction of Carbonyl Compounds
Sarkar, Nabin,Mahato, Mamata,Nembenna, Sharanappa
, p. 2295 - 2301 (2020/05/18)
Two new examples of structurally characterized β-diketiminate analogues i.e., conjugated bis-guanidinate (CBG) supported palladium(II) complexes, [LPdX]2; [L= {(ArHN)(ArN)–C=N–C=(NAr)(NHAr)}; Ar = 2,6-Et2-C6H3], X = Cl (1), Br (2) have been reported. The synthesis of complexes 1–2 was achieved by two methods. Method A involves deprotonation of LH by nBuLi followed by the treatment of LLi (insitu formed) with PdCl2 in THF, which afforded compound 1 in good yield (75 %). In Method B, the reaction between free LH and PdX2 (X = Cl or Br) in THF allowed the formation of complexes 1 (Yield 73 %) and 2 (Yield 52 %), respectively. Moreover, these complexes were characterized thoroughly by several spectroscopic techniques (1H, 13C NMR, UV/Vis, FT-IR, and HRMS), including single-crystal X-ray structural and elemental analyses. In addition, we tested the catalytic activity of these complexes 1–2 for the hydroboration of carbonyl compounds with pinacolborane (HBpin). We observed that compound 1 exhibits superior catalytic activity when compared to 2. Compound 1 efficiently catalyzes various aldehydes and ketones under solvent-free conditions. Furthermore, both inter- and intramolecular chemoselectivity hydroboration of aldehydes over other functionalities have been established.
Method for synthesizing propargyl alcohol
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Paragraph 0041-0042, (2017/09/02)
The invention discloses a method for synthesizing propargyl alcohol. The method includes hydrolyzing 1, 3-dichloropropene in saturated alkali metal carbonate solution to obtain 3-chloropropene alcohol; removing hydrogen chloride from the 3-chloropropene alcohol under the condition of the presence of a polar solvent dimethyl sulfoxide and hydroxide of alkali metal so as to obtain the propargyl alcohol. The method has the advantages that the 1, 3-dichloropropene is used as a raw material, the raw material can come from wide sources, is inexpensive and is easily available, the propargyl alcohol is easy to dehydrate, energy can be saved, and environments can be protected; the propargyl alcohol obtained by the aid of the method is high in yield and purity.