Mass Spectral Interaction between the Functional Groups of Multiply Substituted Alkanes

The mass spectral decomposition of di- and polyfunctional alkanes is characterized essentially by two, fundamentally different reactions: On the one hand the structures of the fragment ions are determined by separated degradation of each functional group; on the other hand, however, a relatively large number of fragment ions result from the combined action of two or even more functional groups. This special type of fragmentation has become an important topic in today's mass spectral research. In the present progress report an attempt has been made to summarize the results obtained so far.

[1]  M. Hesse,et al.  Nachbargruppeneffekte bei der massenspektrometrischen Fragmentierung: N‐Acetyl‐ω‐Phenylalkylamine. 20. Mitteilung über das massenspektrometrische verhalten von stickstoffverbindung , 1974 .

[2]  S. Osman,et al.  The mass spectra of ω‐amino acid derivatives. The role of ω‐activation in production of ions upon electron‐impact , 1973 .

[3]  R. T. Coutts,et al.  The fragmentation of ortho‐methoxyphenyl‐2‐propanone oximes and related compounds–further examples of an ortho‐effect , 1973 .

[4]  D. Kingston,et al.  Intramolecular hydrogen transfer in mass spectra. I. Rearrangements in aliphatic hydrocarbons and aromatic compounds , 1973 .

[5]  M. Hesse,et al.  Chaenorhin, ein macrocyclisches Spermin‐Alkaloid. 149. Mitteilung über Alkaloide , 1973 .

[6]  C. Djerassi,et al.  Mass spectrometry in structural and stereochemical problems—CCXXIII:ortho interactions of nitro groups , 1973 .

[7]  J. Holmes Intramolecular amide‐amide interaction in the mass spectra of some geometric isomers , 1973 .

[8]  G. Englert,et al.  Die Struktur von Maytenin , 1973 .

[9]  M. Hesse,et al.  Nachbargruppenbeteiligung bei massenspektrometrischen Fragmentierungsreaktionen: Spermin-Derivate. 18. Mitteilung über das massenspektrometrische Verhalten von Stickstoffverbindungen†‡ , 1973 .

[10]  M. Hesse,et al.  Macrocyclic spermidine and spermine alkaloids , 1973, Pure and applied chemistry. Chimie pure et appliquee.

[11]  C. Djerassi,et al.  Mass spectrometry in structural and stereochemical problems—CCXIX: Identification of an unidirectional quadruple hydrogen transfer process in 7‐phenylhept‐3‐en‐2‐one o‐methyl oxime ether , 1972 .

[12]  J. Liehr,et al.  The Loss of CH3COCH2 Moieties from Methylketo Esters upon Electron Impact: A discussion of possible long‐range functional group interaction , 1972 .

[13]  W. Richter,et al.  Migration of dimethylsilyl substituents upon electron-impact: The fragmentation of methyl 12-dimethylsilyloxyoctadecanoate , 1972 .

[14]  M. Hesse,et al.  Nachbargruppeneffekte bei massenspektrometrischen Fragmentierungsreaktionen: substituierte 1,3-Diaminopropan-Derivate. 17. Mitteilung über das massenspektrometrische Verhalten von Stickstoffverbindungen†‡ , 1972 .

[15]  G. Eglinton,et al.  The constituent acids of gymnosperm cutins , 1972 .

[16]  F. Benoit,et al.  The mass spectra of carboxylic acids·IV: Carboxyl‐carboxyl interaction in some cycloalkane 1,2 dicarboxylic acids and its relationship with molecular geometry , 1972 .

[17]  F. Benoit,et al.  The mass spectra of carboxylic acids—V: Carboxyl-carboxyl interaction in the fragmentation of some cycloalkene-1,2-dicarboxylic acids , 1972 .

[18]  G. Horváth,et al.  Mechanism of the elimination reactions in α,δ diols and their halogenated derivatives under electron‐impact , 1972 .

[19]  Jerry Ray Dias,et al.  Mass spectrometry in structural and stereochemical problems—CCXVI: Anomalous cleavage ions in bifunctional compounds resulting from participative interaction , 1972 .

[20]  C. Djerassi,et al.  Mass spectrometry in structural and stereochemical problems. CCXV. Behavior of phenyl-substituted .alpha.,.beta.-unsaturated ketones upon electron impact. Promotion of hydrogen rearrangement processes , 1972 .

[21]  M. Hesse,et al.  Charakteristika in den Massenspektren von Spermidin-Derivaten† , 1972 .

[22]  C. Djerassi,et al.  Mass spectrometry in structural and stereochemical problems. CCIX. Functional group interaction after electron impact. Anomalous ether cleavage in bifunctional benzyloxy ethers , 1971 .

[23]  S. Meyerson,et al.  Localized activation in bond-forming reactions under electron impact. Internal solvation in isolated molecules , 1971 .

[24]  M. Hesse,et al.  Neue alkaloide aus Adhatoda vasica Nees , 1971 .

[25]  M. Hesse,et al.  Neuartige massenspektrometrische Zerfallsreaktionen bei α,ω‐disubstituierten Alkanen. 15. Mitteilung über das massenspektrometrische verhalten von stickstoffverbindungen [1] , 1971 .

[26]  J. McCloskey,et al.  Functional Group Interactions in the Mass Spectra of Trimethylsilyl Derivatives of Halo Acids and Halo Alcohols , 1970 .

[27]  G. Spiteller,et al.  Über den Einfluß von Substituenten auf die primären Abbaureaktionen aliphatischer Verbindungen im Massenspektrometer , 1970 .

[28]  R. T. Gray,et al.  Mass spectrometry in structural and stereochemical problems–CLXXXIX: Electron‐impact induced fragmentations and rearrangements of alkoxycyclohexanol trimethylsilyl ethers and alkoxycyclohexyl trimethylsilanes , 1970 .

[29]  J. Kossanyi,et al.  Spectrométrie de Masse—IV: Fragmentation des Dicétones—ϵ† , 1970 .

[30]  P. Potier,et al.  Alcaloïdes de Vepris ampody (Rutacées) , 1970 .

[31]  J. McCloskey,et al.  Fragmentations de Molecules Aliphatiques Bifonctionnelles: Methoxyesters , 1970 .

[32]  C. Djerassi,et al.  Mass spectrometry in structural and stereochemical problems—CXCVII: Electron‐impact induced functional group interaction in 4‐benzyloxycyclohexyl trimethylsilyl ether , 1970 .

[33]  N. Hancox,et al.  New alkaloids of Alstonia constricta , 1970 .

[34]  M. Hesse,et al.  Über das makrocyclische Spermidinalkaloid Inandenin. 138. Mitteilung über Alkaloide. , 1970 .

[35]  T. Shiba,et al.  Structure and synthesis of putreanine. A new amino acid isolated from mammalian brain. , 1970, Tetrahedron.

[36]  F. Benoit,et al.  The mass spectra of carboxylic acids—I: Fragmentation mechanisms in maleic and fumaric acids and related compounds , 1969 .

[37]  M. Hesse,et al.  SN-2-artige massenspektrometrische Fragmentierungen bei substituierten N-Alkylpiperidinen. 10. Mitteilung über das massenspektrometrische Verhalten von Stickstoffverbindungen [1] , 1968 .

[38]  C. Djerassi,et al.  Massenspektrometrie und ihre Anwendung auf strukturelle und stereochemische Probleme CLXVII Langkettige Wasserstoffverschiebung in der Massenspektrometrie , 1968 .

[39]  M. Hesse,et al.  Struktur der makrocyclischen Alkaloide Oncinotin und Iso‐oncinotin. 129. (vorläufige) Mitteilung über Alkaloide , 1968 .

[40]  Dudley H. Williams,et al.  Mass spectrometry. XXX. Substituent effects of mass spectrometry. Comparison of change localization and quasi-equilibrium theories , 1968 .

[41]  C. Djerassi,et al.  Mass spectrometry in structural and stereochemical problems. CXIX. Interaction of remote functional groups in mass spectrometry. , 1966, Journal of the American Chemical Society.

[42]  V. Hanuš,et al.  The structure of glaucamine an alkaloid from Papaver glaucum BOISS. et HAUSKN. Mass spectrometric study of fragmentation of rhoeadine alkaloids , 1965 .

[43]  C. Djerassi,et al.  Mass Spectrometry in Structural and Stereochemical Problems. XXXI.1 Aporphines and Related Alkaloids2 , 1963 .

[44]  G. Spiteller Der o-Effekt in den Massenspektren aromatischer Verbindungen , 1961 .

[45]  K. Biemann,et al.  Mass Spectra of Organic Molecules. I. Ethyl Esters of Amino Acids1 , 1961 .

[46]  Toshio Nakayama,et al.  Ionization Potentials of Some Molecules , 1957 .

[47]  C. D. Hurd,et al.  Ring-Chain Tautomerism of Hydroxy Aldehydes , 1952 .

[48]  M. Stoll,et al.  Vielgliedrige heterocyclische Verbindungen IV. Die annähernd quantitative Lactonisierung von 14-Oxytetradecan-1-carbonsäure u. 15-Oxypentadecan-1-carbonsäure , 1934 .

[49]  K. Ziegler,et al.  Über vielgliedrige Ringsysteme. I. Die präparativ ergiebige Synthese der Polymethylenketone mit mehr als 6 Ringgliedern , 1933 .