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

Autor:	John P. Chupp, John M. Molyneaux, Gina L. Stikes, Y. Larry Sing, Len F. Lee, Scott S. Woodard
Rok vydání:	1990
Předmět:	chemistry.chemical_compound Trifluoromethyl chemistry Organic Chemistry Organic chemistry Tautomer Fluoride Isomerization
Zdroj:	The Journal of Organic Chemistry. 55:2872-2877
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00296a058
Popis:	A series of 2-(trifluoromethyl)-1,4- and -3,4-dihydro-3,5-pyridinedicarboxylates 5a-y and 6a-y undergo an unprecedented dehydrofluorination upon treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), trialkylamines, or 2,6-lutidine to give the corresponding 2-(difluoromethyl)-3,5-pyridinedicarboxylates 8a-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-dihydropyridines 16t followed by elimination of fluoride from 13a-y or 14a-y or dehydrofluorination of 16t
Databáze:	OpenAIRE
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