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Nucleophilic Intramolecular Cyclization Reactions of Alkynechalcogenolates

✍ Scribed by M.A. Abramov; W. Dehaen; B. D'hooge; M.L. Petrov; S. Smeets; S. Toppet; M. Voets


Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
137 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis


AbstractÐ2-(ortho-Hydroxyphenyl)-alkynethiolates and -selenolates, obtained through base catalyzed ring cleavage of 4-(ortho-hydroxyphenyl)-1,2,3-thiadiazoles and -1,2,3-selenadiazoles, smoothly transform into 2-benzofuranthiolates and -selenolates. These reactive intermediates can be alkylated in high yield. This reaction sequence could be applied to the synthesis of electron rich thiacrown ethers. The 2-(ortho-aminophenyl)-alkynethiolate analogously forms 2-methylsulfanylindole.


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