A General, Stereospecific Synthetic Route to π2-Thiazolines

GK Helmkamp, DJ Pettitt, JR Lowell Jr…

Index: Helmkamp,G.K. et al. Journal of the American Chemical Society, 1966 , vol. 88, p. 1030 - 1033

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Citation Number: 21

Abstract

Abstract: A new route to A2-thiazolines is presented, consisting of treatment of an episulfide with a nitrile in the presence of a strong acid. The stereospecificity of the reaction is shown by production of isomeric thiazolines from cis-and trans-2-butene episulfides. The reaction is successful with either alkyl or aryl nitriles and gives moderate yields even with hindered nitriles. Polymerization of the episulfide is a competing reaction and predominates in the ...