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The hydrohalogenation reaction of 1-alkyl substituted 1,2-allenyl carboxylic acid esters (1) with MX (M= Na, or Li, X= Cl, Br, I) afforded a mixture of (5,7-unsaturated 3-halo-3-alkenoates (2) and α,β-unsaturated 3-halo-2-alkenoates (3) in HOAc, while using a mkture of HOAc-CF3CO2H (1:1) or CF3CO2H as the reaction medium the corresponding reaction cleanly produced β,γ-unsaturated 3-halo-3-alkenoates (2) as the sole products in high yields. The subsequent coupling reactions were studied. 相似文献
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Kazuhiro Ohashi Shigenori MiharaAkihiro H. Sato Masataka IdeTetsuo Iwasawa 《Tetrahedron letters》2014
A convenient synthesis of 1-haloethenamides has been achieved by utilizing halotrimethylsilane (TMSX, X = Cl, Br, I) and water. Halotrimethylsilane in 1 M CH2Cl2 solution functions as a halogen source of the in situ generated HX, and the HX added to the terminal triple bonds of ynamides in Markovnikov fashion. 相似文献
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Stereospecific hydrohalogenation reactions of electron-deficient alkynes,i.e.,2-alkynoic acids,2-alkynoates,2-propynamides,2-propynenitrile,1-alkynyl phosphonates/phosphine oxides,1-alkynyl sulfoxides/triflones,and 1-alkynyl iodonium salts with lithium or sodium halides to afford Z-alkenyl derivatives and their applications in synthesis of important intermediates as well as natural products were reviewed. 相似文献
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A simple protocol for regio-, and stereoselective hydrohalogenation of ynamide moieties in 1,3-butadiyne structures is described. The facile approach enables exact syn-addition of HX to the diyne components, giving just single isomer of the corresponding dienes and enynes. 相似文献
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