A novel dehydrofluorination of 2-(trifluoromethyl) dihydro-3, 5-pyridinedicarboxylates to 2-(difluoromethyl)-3, 5-pyridinedicarboxylates

LF Lee, GL Stikes, JM Molyneaux, YL Sing…

Index: Lee, Len F.; Stikes, Gina L.; Molyneaux, John M.; Sing, Y. Larry; Chupp, John P.; Woodard, Scott S. Journal of Organic Chemistry, 1990 , vol. 55, # 9 p. 2872 - 2877

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Citation Number: 29

Abstract

A series of 2-(trifluoromethyl)-l, 4-and-3, 4-dihydro-3, 5-pyridinedicarboxylates 5a-y and 6a-y undergo an unprecedented dehydrofluorination upon treatment with l, &diazabicyclo [5.4. 0] undec-7-ene (DBU), trialkylamines, or 2, 6-lutidine to give the corresponding 2- (difluoromethyl)-3, 5-pyridinedicarboxylates Sa-y. This novel reaction is believed to involve isomerization of 5a-y and 6a-y to the tautomeric anions 13a-y and 14a-y or the 1, 2- ...