Gas-phase alkylation of 2-methylfuran under chemical ionization conditions

In the gas phase, under chemical ionization conditions, the sites of attachment of [CH3]+ and [C2H5]+ to 2-methylfuran have been studied by tandem mass spectrometry. Spontaneous metastable and collision-induced fragmentations have been compared to those observed for the protonated alkylfuran isomers. The results obtained show that alkylation occurs preferentially at the β-position.

[1]  H. Audier,et al.  Competing rearrangement reactions of protonated methylfuran , 1986 .

[2]  A. G. Harrison.  Site of gas-phase ethyl ion attachment , 1986 .

[3]  R. Cooks,et al.  Charge stripping and the site of cationization of substituted aromatic compounds , 1986 .

[4]  R. Houriet,et al.  Gas‐Phase Basicities of Furan Compounds. The Role of Alkyl Substitution on Proton Affinity and on the Site of Protonation , 1985 .

[5]  G. Angelini,et al.  GAS-PHASE HETEROAROMATIC SUBSTITUTIONS. 5. GAS-PHASE PROTONATION OF FIVE-MEMBERED HETEROAROMATIC RINGS BY HYDRO-T-HELIUM(1+)-3HE (3HET+) IONS. A MODEL REACTION FOR A THEORETICAL APPROACH TO HETEROAROMATIC REACTIVITY , 1984 .

[6]  H. Audier,et al.  Isomerisation des ions alkyl-furannes et alkyl-pyrannes protones en phase gazeuse , 1984 .

[7]  R. Cooks,et al.  Site of gas-phase cation attachment. Protonation, methylation, and ethylation of aniline, phenol, and thiophenol , 1983 .

[8]  A. Margonelli,et al.  Gas-phase heteroaromatic substitution. Part 4. Electrophilic attack of t-butyl cation on pyrrole, N-methylpyrrole, furan, and thiophene , 1983 .

[9]  G. Angelini,et al.  Gas-phase heteroaromatic substitution. 3. Electrophilic methylation of furan and thiophene by CH/sub 3/XCH/sub 3//sup +/ (X = F or Cl) ions , 1982 .

[10]  G. Angelini,et al.  Gas-phase heteroaromatic substitution. 2. Electrophilic methylation of pyrrole and N-methylpyrrole by CH3XCH3+ (X = fluoro, chloro) ions , 1982 .

[11]  J. D. Morrison,et al.  The reaction of CH4+, CH3+, and other simple carbocations with benzene in the gas phase , 1981 .

[12]  J. Beynon,et al.  The gas phase structure of some protonated and ethylated aromatic amines , 1980 .

[13]  F. H. Field.  Chemical ionization mass spectrometry. VI. C7H8 isomers. Toluene, cycloheptatriene, and norbornadiene , 1967 .