The fluorination of cyclopentadiene and 3,4-epoxycyclopentene

Autor:	Robert D. Chapman, Michael Chua Chiaco, Victor L. Heasley, Kelly M. Gallego, William S. C. Low, Barbara Carter, Dale F. Shellhamer
Rok vydání:	1995
Předmět:	Cyclopentadiene Organic Chemistry Xenon difluoride Difluoride Epoxide Biochemistry Inorganic Chemistry chemistry.chemical_compound Trifluoride chemistry Reagent Environmental Chemistry Organic chemistry Pyridinium Physical and Theoretical Chemistry Fluoride
Zdroj:	Journal of Fluorine Chemistry. 72:83-87
ISSN:	0022-1139
DOI:	10.1016/0022-1139(94)03190-b
Popis:	Cyclopentadiene (1) was treated with xenon difluoride and (difluoroiodo)benzene to give trans- and cis-3,4-difluorocyclopentenes (2,3) and trans- and cis-1,4-difluorocyclopentenes (4,5). Reaction of 3,4-epoxycyclopentene (6) with pyridinium polyhydrogen fluoride gave four fluorohydrins which were converted with diethyiaminosulfur trifluoride (DAST) to the difluorocyclopentenes 2-5. The best yield (50%) of the difluorocyclopentenes was from the reaction of DAST with epoxide 6. Synthesis and isolation of these labile difluorides of cyclopentenes (2-5) demonstrate the mild nature of these fluorinating reagents.
Databáze:	OpenAIRE
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