Novel Synthetic Chemistry of Ureas and Amides by Marc Hutchby

Author:Marc Hutchby
Language: eng
Format: epub
Publisher: Springer Berlin Heidelberg, Berlin, Heidelberg

The drop in reactivity is substantial, with several mechanistic implications possible. Perhaps the electron donating methyl group does not allow for facile deprotonation, or the methyl group may facilitate a change in conformation of the molecule disrupting any twisting effect, necessary for the reactivity shown.

Following this successful study, alternative electron withdrawing groups were investigated. Interestingly triflouropropionamides failed to yield any methyl ester when the N-tert-butyl-iso-propyl (133) was employed (Scheme 5.7).

Scheme 5.7Methanolysis resistant triflouropropionamide derivative

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