2007
DOI: 10.1134/s1070428007050107
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Reactions of acetylene ketones in superacids

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Cited by 26 publications
(13 citation statements)
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“…Moreover, triflic acid was also found to promote the hydroarylation reaction to some extent in the absence of Pd complex catalysts. [19] A conversion of 14 % with 64 % selectivity for the Z product was recorded after 24 h. In contrast, neither tetrafluoroboric acid nor trifluoroacetic acid promoted the formation of hydroarylation products with ethyl propiolate in the absence of a Pd catalyst.…”
Section: Effect Of Acid and Conjugated Basementioning
confidence: 99%
“…Moreover, triflic acid was also found to promote the hydroarylation reaction to some extent in the absence of Pd complex catalysts. [19] A conversion of 14 % with 64 % selectivity for the Z product was recorded after 24 h. In contrast, neither tetrafluoroboric acid nor trifluoroacetic acid promoted the formation of hydroarylation products with ethyl propiolate in the absence of a Pd catalyst.…”
Section: Effect Of Acid and Conjugated Basementioning
confidence: 99%
“…A general approach to the alkenylation of arenes with aryl acetylenes conjugated with electron-withdrawing groups, under superacidic conditions, was presented in a series of reports. Vinyl dications 530 , generated upon protonation of the electron-withdrawing substituent and the CC triple bond of compounds 529 , react with arenes, furnishing products of arene alkenylation 531 , as E- or Z- isomers (Scheme ).…”
Section: Bro̷nsted-acid-promoted Reactionsmentioning
confidence: 99%
“…For example, 1,3,3-triphenylprop-2-en-1-one failed to react with benzene in the presence of AlCl 3 and HCl [21]. Moreover, in the present work we also found that a ~1 : 1 mixture of (E)-and (Z)-4-(4-methylphenyl)-4-phenylbut-3-en-2-ones [22] remained unchanged after heating for 0.5 h at 60°C in benzene in the presence of AlBr 3 (according to the general procedure for the reaction of acetylenic compounds with arenes; see Experimental) and was quantitatively recovered from the reaction mixture. No structures like XII were detected in analogous reactions of acetylenic compounds Ia-Ih (see below).…”
mentioning
confidence: 76%
“…The syntheses and properties of the other acetylenic substrates, 4-(4-methylphenyl)but-3-yn-2-one (Ic), 4-phenylbut-3-yn-2-one (IIb), 4-(2,4-dimethylphenyl)but-3-yn-2-one (Id), 4-(4-methoxyphenyl)but-3-yn-2-one (If) [40], 4-(2,4,6-trimethylphenyl)-but-3-yn-2-one (Ie) [22]; 1,3-diphenylprop-2-yn-1-one (Ih) [41]; 2,4-diphenylbut-3-yn-2-ol (IIa), 1,1,3-triphenylprop-2-yn-1-ol (IIf), 2-methyl-4-(4-methylphenyl)but-3-yn-2-ol (IIg) [17], 3-(4-fluorophenyl)-propynoic acid (IIIb), 3-(4-methylphenyl)propynoic acid (IIIc) [42], methyl 3-phenylpropynoate (IVa), and methyl-3-(4-methylphenyl)propynoate (IVb) [43] were reported previously.…”
Section: Methodsmentioning
confidence: 99%