The integrated peak intensity in 19F NMR spectra as a function of time for the reaction of styrene 1a with pyrrolidine

July 23, 2024

• Title:       

  The integrated peak intensity in 19F NMR spectra as a function of time for the reaction of styrene 1a with pyrrolidine

• Image Source:

  Mechanistic study of multi-step nucleophilic substitution for trifluoromethylated styrenes

• Mark:

  Fig. 1

• Associated context:

  The kinetic of the reaction obtained by 19F NMR reveals the simultaneous disappearance of E- and Z-isomers of 1a and formation of 2a as the mixture of E- and Z-isomers (Fig. 1). Any other signals were not observed during all time of the monitoring.  Similar to secondary amines, isopropyl- or cyclohexylamine react with styrene 1a very easily at room temperature. But in these cases, the enamines 2b,c are formed along with their tautomers 3a,b (see  Supporting Information, Section 1.2). unexpected products of nucleophilic C–F bond cleavage (primary or secondary amines) or fragmentation (binucleophiles) (Scheme 2).