118948-70-2Relevant academic research and scientific papers
Phosphonium salt catalyzed addition of diethylzinc to aldehydes
Werner, Thomas,Riahi, Abdol Majid,Schramm, Heiko
, p. 3482 - 3490 (2011)
The addition of diethylzinc to aromatic, heteroaromatic, and aliphatic aldehydes at room temperature is efficiently catalyzed by 1-7 mol% tetrabutylphosphonium chloride. The corresponding addition products are obtained in good to excellent yields of up to 99%. Moreover, polymer bond phosphonium salts can be used to catalyze this reaction with excellent recovery of the polymer bond catalyst up to three cycles. The application of chiral bifunctional phosphonium salts revealed a remarkable counter anion effect. Changing the anion, the activity of the tetrabutylphosphonium salt decreased in the order Cl- > Br- > I- ≈ TsO- > BF4- ≈ PF6-. However, the nature of the cation had also significant influence. Tetraalkyl-ammonium chlorides showed similar activity compared to phosphonium chlorides, while alkaline metal chlorides proved to be considerably less active. Georg Thieme Verlag Stuttgart.
Estimation of Reduction and Standard Potentials of Some Allyl and Substituted Alkyl Radicals
Occhialini, Donatella,Kristensen, Jesper S.,Daasbjerg, Kim,Lund, Henning
, p. 474 - 481 (2007/10/02)
Anion radicals of aromatic compounds react with alkyl halides by dissociative electron transfer, the radicals thus formed may either couple with the anion radicals or may be reduced by the anion radicals.The competition between the coupling and the reduction may be used to determine the reduction potential and standard potential of the radicals.In this report the results concerning the redox properties of allyl radicals and different kinds of alkyl radical, such as methyl, ethyl and propyl, very sterically hindered alkyl radicals and 2-methoxy-substituted cycloalkyl radicals, are presented.The standard potentials of the allyl radicals are between -1.39 and -1.72 vs.SCE.For most of the alkyl radicals the interval is from -1.63 to -1.81 V.However, the potential of the methyl radical is, quite unexpectedly, found by this method to be approximately 400 mV more positive than the potential of a primary alkyl radical and even more positive than that of the benzyl radical.
MERCURATION OF ALKYLCYCLOPROPANES WITH ELECTRON-ACCEPTING SUBSTITUENTS IN THE AROMATIC RING
Bandaev, S. G.,Eshnazarov, Yu. Kh.,Nasyrov, I. M.,Mochalov, S. S.,Shabarov, Yu. S.
, p. 659 - 663 (2007/10/02)
The reactions of (nitrophenyl)- and (acetylphenyl)cyclopropanes with mercuric nitrate and acetate in methanol, acetic acid, and formic acid were studied.The arylcyclopropanes are mercurated by mercuric acetate in formic acid or by mercuric nitrate in all the employed solvents without a catalyst (perchloric acid).A relatively high rate of conjugate mercuration of arylcyclopropanes in formic acid was observed.
