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Trifluoropropene electrophilic addition

Addition of hydrogen halides across the double bond in perfluoropro-pene resembles the addition to 3,3,3-trifluoropropene. Here, too, fluorines drain electrons from the double bond, rendering it electron-poor, which means that electrophilic additions of hydrogen halides are very difficult. Electron density of the double bond is distributed in such a way that the partial negative charge is at the carbon adjacent to the trifluoromethyl group. Consequently, the proton of the hydrogen halides joins... [Pg.53]

The orientation of electrophilic addition to trifluoropropene was originally thought to be a reflection of the relative stabilities of the intermediate carbocations 4.15A and 4.15B (Figure 4.15), but it was subsequently found that trifluoropropene is dimerised, rather than protonated in highly acidic media [47, 48]. Deuterium labelling studies indicated that the reaction proceeds via initial fluoride ion abstraction to yield an intermediate allyl cation [49] (Figure 4.16). [Pg.101]

The electrophilic addition of chlorosulfonic acid to 3,3,3-trifluoropropene 15 was foimd to yield mainly 3-chloro-l,l-difluorochlorosulfonate 16 (Equation 5). °... [Pg.149]

The electrophilic addition of HCl to 3,3>3-trifluoropropene gives l-chloro-3,3.3-trifluoropropane, an ft -Markovnikov addition product. Consider the structure of the intermediate carbocations possible for the two modes of addition and suggest a... [Pg.218]

Systems with perfluoroalkyl groups directly attached to the double bond are particularly unreactive towards electrophiles but reaction of hexafluoropropene (HFP) with SbFs leads to a perfluoroallyl cation, which then reacts with another molecule of HFP to give a dimer, probably by an electrophilic process [168] (Figure 7.51) that is analogous to that described earlier for 1,1,1-trifluoropropene [169], (Chapter 4, Section VIB). Similar addition and isomerisation reactions, which proceed via carbocationic intermediates, are given in Figure 7.52 [170-172]. [Pg.194]


See other pages where Trifluoropropene electrophilic addition is mentioned: [Pg.1833]    [Pg.24]    [Pg.64]    [Pg.53]   
See also in sourсe #XX -- [ Pg.102 ]




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3,3,3-Trifluoropropenes

3.3.3- trifluoropropene

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