2009
DOI: 10.1016/j.tet.2009.08.005
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Recent progress in the use of fluoroorganic compounds in pericyclic reactions

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Cited by 38 publications
(16 citation statements)
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References 183 publications
(170 reference statements)
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“…Cyclization of 1 with the a-imines (2) was accomplished in 65 and 77% yield by refluxing the components in toluene with silver acetate catalyst to give 4a and 4b.…”
mentioning
confidence: 99%
“…Cyclization of 1 with the a-imines (2) was accomplished in 65 and 77% yield by refluxing the components in toluene with silver acetate catalyst to give 4a and 4b.…”
mentioning
confidence: 99%
“…In the presence of excess base (5 equiv KOtBu), deprotonation and formation of a short-lived p-allyl potassium complex [29] occurs, and collapses to C. Intermediate C (not directly detectable) contains a gemdifluorohexatriene motif, which undergoes a 6p electrocyclization to produce D. [30] Although general studies regarding the influence of fluorine substituents on 6p electrocyclizations are not available, it is known that fluoroorganic compounds show increased reaction rates for many pericyclic reactions. [31] However, the opposite effect was observed for the thermal rearrangement of polyfluorinated substrates, such as 9,10-bis(trifluorovinyl)pheanthrene. [32] Loss of a second equivalent of potassium fluoride and rearomatization gives E. For the conver- Scheme 1.…”
Section: Resultsmentioning
confidence: 99%
“…Dipolar cycloaddition reactions of fluoroalkenes [65][66][67] provide new methods of preparation of heterocycles with fluorinated groups, which are substances of increasing practical importance [68][69][70][71][72][73]. Cycloaddition of pyridine N-oxides with hexafluoropropene (C 3 F 6 , HFP) has been reported already in the 1960s by Mailey Scheme 11 Cu-catalyzed cycloaddition of quinazoline 3-oxides and alkylidenecyclopropanes followed by heterocyclic ring opening [64] and Ocone as a reaction proceeding in an autoclave at elevated temperature and pressure to give 2-(1,2,2,2-tetrafluoroethyl)pyridines.…”
Section: Cycloaddition To Carbon-carbon Multiple Bondsmentioning
confidence: 99%