2015
DOI: 10.1134/s1070428015020086
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Nucleophilic addition to acetylenes in superbasic catalytic systems: XVIII. Vinylation of phenols and naphthols with acetylene

Abstract: Phenols and naphthols react with acetylene in a superbasic system KOH-DMSO forming the corresponding aryl vinyl ethers in up to 80% yields. * For communication XVII, see [1].Aryl vinyl ethers compared with aliphatic analogs are more stable against hydrolysis and are more reactive in the radical polymerization. They are highly reactive building blocks for organic synthesis. The pioneering research in this field was carried out by the scientific school of A.V. Kalabina [2-4] who widely used aryl vinyl ethers for… Show more

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Cited by 13 publications
(3 citation statements)
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“…[16] On the other hand, aryl vinyl ethers serve as i) valuable intermediates in various reactions, [17] ii) precursors for polymeric materials, [18] and iii) as phenolic protecting groups [19] in organic synthesis. [31] However, the above mentioned methods for the synthesis of N-vinylpyrole and aryl vinyl ether have some drawbacks. An alternative method for N-vinylation of indoles involves the use of 1,2-dichloroethane in the presence of phase transfer catalyst.…”
Section: Introductionmentioning
confidence: 99%
“…[16] On the other hand, aryl vinyl ethers serve as i) valuable intermediates in various reactions, [17] ii) precursors for polymeric materials, [18] and iii) as phenolic protecting groups [19] in organic synthesis. [31] However, the above mentioned methods for the synthesis of N-vinylpyrole and aryl vinyl ether have some drawbacks. An alternative method for N-vinylation of indoles involves the use of 1,2-dichloroethane in the presence of phase transfer catalyst.…”
Section: Introductionmentioning
confidence: 99%
“…Significant progress in the intermolecular nucleophilic addition of alcohols onto alkynes by using base was made by Kondo, Knochel (Scheme , i), and Minidis . In 2015, Trofimov reported the base‐mediated reaction of phenols with acetylene (Scheme , ii). In 1998, Teles and co‐workers reported the formation of alkoxyalkanes and enol ethers by the direct addition of alcohols to alkynes by using cationic gold(I) .…”
Section: Introductionmentioning
confidence: 99%
“…[25][26][27][28][29][30][31][32][33][34][35][36] Since the first synthesis of 4-vinyloxy-TEMPO, 24 no attempt to develop an expedient hydroalkoxylation of alkynes with 4-hydroxy-TEMPO has been undertaken. Meanwhile, having in mind that direct superbasecatalyzed hydroalkoxylation of alkynes with hydroxyl compounds has proved to be highly efficient, [37][38][39][40][41][42] we decided to revisit the vinylation of 4-hydroxy-TEMPO with various alkynes exploiting our expertise gained during the last decade.…”
Section: Introductionmentioning
confidence: 99%