Cycloalkene budding: mass spectrometric studies of competitive and dual cycloalkene extrusion reactions from doubly unsaturated aldehyde N,N-dimethylhydrazones.

@article{Weibel2000CycloalkeneBM,
  title={Cycloalkene budding: mass spectrometric studies of competitive and dual cycloalkene extrusion reactions from doubly unsaturated aldehyde N,N-dimethylhydrazones.},
  author={D B Weibel and Athula B. Attygalle and Laura Shevy and Jerrold Meinwald},
  journal={Rapid communications in mass spectrometry : RCM},
  year={2000},
  volume={14 13},
  pages={
          1105-9
        }
}
Mass spectral fragmentation pathways of four doubly unsaturated aldehyde N,N-dimethylhydrazones were investigated using EI-MS and tandem mass spectrometry (MS/MS) under electron ionization and collisionally activated decomposition (CAD) conditions. Cyclopentene extrusion was found to be slightly favored over cyclohexene loss in a hydrazone capable of losing either cycloalkene. Evidence for the regeneration of a chain-shortened iminium radical cation as a result of cycloalkene extrusion was… 
2 Citations

References

SHOWING 1-10 OF 49 REFERENCES
Acetonitrile chemical ionization tandem mass spectrometry to locate double bonds in polyunsaturated fatty acid methyl esters.
TLDR
Fragmentation of polyene FAME yields major diagnostic ions resulting from cleavage between double bonds that appear one mass unit lower, and the method is shown to produce highly characteristic spectra for FAME with 1 to 6 double bonds.
Theoretical reaction paths for cation radical cycloadditions : The [3+2] or role-reversed cation radical diels-alder
Abstract An extended basis set ab initio reaction path calculation for the prototype role-reversed cation radical Diels-Alder reveals that even this symmetry-forbidden cyclization mode proceeds
CBS-4 ab initio results on the formation and stability of N-aminoazetidine radical cation and derivatives
Abstract Experimental evidence has recently indicated the role of substituted azetidine radical cations in the electron ionization (EI) mass spectrometric fragmentation of N , N -dimethylhydrazone
Ion-molecule reactions and collision-activated dissociation of C4H4+. isomers: A case study in the use of the MS3 capabilities of a pentaquadrupole mass spectrometer
TLDR
The unique combination of ion-molecule reactions with collision-activated dissociation employed here provides valuable information on the chemistry of ionized cyclobutadiene, including its proclivity to undergo [2 + 2?] and [4 + 2] cyc1oadditions.
Reactivity of vinylamine radical cation with neutral olefins: an example of ionic' free-radical chemistry in the gas phase
Hydrogen atom abstraction and cycloaddition–cycloreversion reactions between ionized vinylamine and neutral olefins were studied in a Fourier transform ion cyclotron resonance spectrometer. The
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
[2+1] cycloaddition of ketene radical cation and ethylene
La reaction est etudiee par spectrometrie de masse tandem et par spectrometrie de masse avec transformee de Fourier. La structure du compose d'addition est celle d'un cation radicalaire de
Competing hole catalyzed diels-alder and cyclobutanation/vinylcyclobutane rearrangement paths. A mechanistic dichotomy
Etude cinetique de la cycloaddition du (phenyl vinyl) sulfure et du 1,1'-bicyclopentenyle catalysee par le tris(4-bromophenyl) aminium hexachloroantimoniate
[2 + 2 + 2] Cycloadditions
This section will address transition metal mediated cycloaddition processes that fall into the [2 + 2 + 2] category: reactions involving three components, each of which formally contributes two
Photosensitized cyclodimerization of phenyl vinyl ether
Irradiation of phenyl vinyl ether in the presence of aromatic compounds, such as dimethyl terephthalate, methyl benzoate, or benzonitrile, gives a mixture of trans- and cis-head-to-head cyclodimers
...
1
2
3
4
5
...