Interaction of hexafluoropropene trimers with ammonia and primary amines

Experimental and Computational Study of the Conrotatory Ring Opening of Various 3-Chloro-2-azetines

“…A series of 4-functionalized 2,3,4-tri- tert -butyl-2-azetines, as intermediates in the synthesis of 2 H -pyrroles, 1,3-butadienes, and 2-aza-1,3-butadienes, has been reported from addition reactions of tri- tert -butylazete while perfluorinated alkenes reacted with amines to give a variety of perfluorinated 2,3,4,4-tetraalkyl-2-azetines . It was envisaged that 2,4-disubstituted 3,3-dichloroazetidines could be precursors for the convenient preparation of synthetically valuable 2,4-disubstituted 3-chloro-2-azetines.…”

Three-Component Bisannulation for the Synthesis of Trifluoromethylated Tetracyclic Aza-Aromatics through Six C(sp3)–F Bond Cleavage and Four C–N Bond Formation

“…On the basis of these obtained results, a proposed mechanism is outlined in Scheme . − Initially, a successive defluorination of perfluoroalkyl substrate 1 under the effect of the alkali-metal base gives unstable naphthalen-1­(4 H )-one intermediate B , which further undergoes the condensation with benzamidine 2 to afford the imine species C . The following intramolecular defluorinative amination of resultant intermediate C through 7- endo-trig cyclization furnishes the ring-closure product E .…”

“…Recently, our laboratory has leveraged the distinctive fluorine effect for heteroannulation, where the synthetic linchpin for realizing the assembly of fluoro-organic molecules is controlled by successive selective defluorination at different centers. − Reactive quinoid species are key intermediates for the C–F bond functionalization and heterocycle construction. Although the reactions of perfluoroalkyl ketones with amidines to form pyrimidine derivatives have been well studied, the accurate six C­(sp 3 )–F bond cleavage at three different sites by using these quinoid species has never been reported until now . Further expansion of multiple C–F bond cleavage manifolds and the pursuit of green and sustainable chemistry have urged us to seek innovative routes for exploiting perfluorinated chemicals.…”

New strategies for the synthesis of 1- and 2-azetines and their applications as value-added building blocks

“…4F) undergo a rearrangement to afford a fluorinated azetidine product (52) with an exocyclic π-bond under basic conditions. 78 Petrov and colleagues similarly identified that fluori-nated tricyclic 1-azetines react with CF 3 Si(CH 3 ) 3 at the imine bond in the presence of cesium fluoride to produce further fluorinated azetidine products. 79 The importance of fluorinated compounds in medicinal chemistry is extensively documented, [80][81][82][83][84][85][86] which highlights the potential applications of these base-driven reactions.…”