Reactivity of vinylamine radical cation with neutral dienes

The gas-phase ion-molecule reactions between ionized vinylamine ([CH 2 =CHNH 2 ] +. ) as a set of conjugated and unconjugated dienes were studied by Fourier transform is observed. Conjugated dienes lead to the elimination of NH 3 or of an hydrocarbon radical from the adduct [M + CH 2 =CHNH 2 ] +. . In the case of unconjugated dienes a regiospecific cyclobutanation-cycloreversion process is observed. Reaction mechanisms are proposed to explain these experimental findings

[1]  S. Hammerum,et al.  Addition of alkenes to phenyl‐substituted enol radical cations, C6H5C(OH)CHR+˙ , 1993 .

[2]  G. Bouchoux,et al.  Reactivity of vinylamine radical cation with neutral olefins: an example of ionic' free-radical chemistry in the gas phase , 1993 .

[3]  G. Bouchoux,et al.  A fourier transform‐ion cyclotron resonance study of the reactivity of ionized vinylalcohol with selected unsaturated compounds , 1990 .

[4]  K. Houk,et al.  Transition structures for hydrogen atom transfers to oxygen. Comparisons of intermolecular and intramolecular processes, and open- and closed-shell systems , 1990 .

[5]  S. Hammerum,et al.  The reactions of enol radical cations with propene in the gas phase , 1990 .

[6]  J. Tortajada,et al.  Structure et role des complexes ions/molecules durant le rearrangement de McLafferty: etude ab initio du systeme [CH2CHOH]+·/CH2CH2 , 1989 .

[7]  K. Houk,et al.  The relationship between proximity and reactivity. An ab initio study of the flexibility of the OH.bul. + CH4 hydrogen abstraction transition state and a force-field model for the transition states of intramolecular hydrogen abstractions , 1988 .

[8]  L. Radom,et al.  Intramolecular hydrogen migration in ionized amines: a theoretical study of the gas-phase analogs of the Hofmann-Loeffler and related rearrangements , 1987 .

[9]  K. Wanczek,et al.  External generation of ions in ICR spectrometry , 1985 .

[10]  P. Carrupt,et al.  Molecular Ions of Transient Species: Vinylamine‐Cation , 1984 .

[11]  D. Golden,et al.  Hydrocarbon Bond Dissociation Energies , 1983 .

[12]  Timothy A. Su.  Chapter 3 – Classical ion–molecule collision theory , 1979 .

[13]  M. Bowers,et al.  Ion-Polar molecule collisions: the effect of ion size on ion-polar molecule rate constants; the parameterization of the average-dipole-orientation theory , 1973 .

[14]  B. Rabinovitch,et al.  ISOMERIZATION OF VIBRATIONALLY EXCITED ALKYL RADICALS BY H-ATOM MIGRATION. , 1970 .

[15]  A. Fish.  Radical rearrangement in gas-phase oxidation and related processes , 1964 .