- Alkylation of 5-Substituted Tetrazoles with Various Alcohols in 1,2-Dichloroethane in the Presence of BF3·Et2O
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Abstract: The alkylation of 1H-tetrazole, 5-methyl-1H-tetrazole, and 5-phenyl-1H-tetrazole with primary, secondary, and tertiary alcohols, including benzylic and allylic ones, have been studied in 1,2-dichloroethane in the presence of boron trifluoride–diethyl ether complex. Neither primary nor secondary saturated alcohols alkylated tetrazoles in the given system. Tertiary alcohols such tert-butyl alcohol and adamantan-1-ol reacted with unsubstituted and 5-substituted tetrazoles to give 70–85% of the corresponding 2-alkyl-5-R-tetrazoles with high regioselectivity. The alkylation of 1H-tetrazole with benzyl alcohol afforded 55% of 2-benzyl-2H-tetrazole as the only product. The alkylation of 1H-tetrazole with various allylic alcohols led to the formation of mixtures of 2-alkyl-2H-tetrazoles with isomeric alkyl substituents.
- Egorov, S. A.,Ishchenko, M. A.,Ivanova, V. I.,Prokopovich, Ya. V.
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p. 1196 - 1203
(2020/10/02)
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- Synthesis of 2-Hydroxybut-3-enylglucosinolate (Progoitrin)
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A synthesis of 2-hydroxybut-3-enylglucosinolate (progoitrin) is described.Its properties and authentication of its biological activity are discussed.This is the first time that this particular glucosinolate has been isolated in pure form by synthesis.
- MacLeod, Alexander J.,Rossiter, John T.
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p. 717 - 721
(2007/10/02)
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