Predominant oxygen-18 exchange accompanying the base hydrolysis of a tertiary toluamide: N-ethyl-N-(trifluoroethyl) toluamide. Assessment of the factors that …

H Slebocka-Tilk, AJ Bennet, HJ Hogg…

Index: Slebocka-Tilk; Bennet; Hogg, Heather J.; Brown Journal of the American Chemical Society, 1991 , vol. 113, # 4 p. 1288 - 1294

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Citation Number: 39

Abstract

Abstract: The hydrolysis of N-ethyl-N-(trifluoroethyl) toluamide (Ill) in basic media at 100" C (p= 1.0 (KCI)) is reported.'* O exchange in 111 recovered from the hydrolytic medium is observed: kex/khyd= 33.4 i 1.6 and is independent of [OH-]. The low basicity of the amine in 111 (pK,(H2+ N (Et) CH2CF,)= 6.3) leads to 2300-3500-fold more exchange in 111 relative to N, N-dimethyltoluamide (I) or N-toluoylpyrrolidine (11). These findings indicate that ...