Protonation of 3-arylpropynoic acid derivatives in superacids

S Walspurger, AV Vasil'ev, J Sommer, P Pale…

Index: Walspurger; Vasil'ev; Sommer; Pale; Savechenkov; Rudenko Russian Journal of Organic Chemistry, 2005 , vol. 41, # 10 p. 1485 - 1492

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Citation Number: 17

Abstract

Abstract According to the 1 H and 13 C NMR data, 3-arylpropynoic acids and their esters XC 6 H nC≡ C-CO 2 R (R= H, Me, Et) having electron-withdrawing substituents in the benzene ring (X= NO 2, CN, COMe, CO 2 Me) exist in HSO 3 F at− 80 to 0° C as XC 6 H nC≡ CC+(OH) OR ions. Derivatives with other substituents (X= H, F, Me, MeO) in HSO 3 F or CF 3 SO 3 H above− 40° C undergo protonation at the acetylenic carbon atom neighboring to ...

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