Reactions of 2-Alkoxypropenals with Thiols in Neutral and Acid Media
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- Keiko, N.A., Funtikova, E.A., Stepanova, L.G. et al. Russian Journal of Organic Chemistry (2002) 38: 970. doi:10.1023/A:1020893310626
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Addition of thiols to 2-alkoxypropenal in neutral medium at 20°C in the absence of a catalyst occurs regioselectively, following the Markownikoff pattern. The resulting 2-alkoxy-2-R-thiopropanals are capable of undergoing spontaneous isomerization to 1-alkoxy-1-R-thiopropanones. The addition and isomerization processes are accelerated by heating to 60°C or in the presence of acid catalysts (TsOH, HCl). The reaction is also accompanied by partial disproportionation of 2-oxopropanal O,S-acetals to give O,O- and S,S-acetals.