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The McLafferty rearrangement: A personal recollection

  • Nico M. M. Nibbering
Focus: McLafferty Rearrangement Account And Perspective

Abstract

In this article, dedicated to Professor Fred McLafferty, I wish to recollect early observations with regard to the rearrangement named after him for 1-nitropropane and the methyl ester of γ-nitrobutyric acid. This rearrangement occurs for both cases clearly in a stepwise fashion, although for the ester, it occurs as a hidden rearrangement that catalyzes the tautomerization of the nitro group into its aci-form.

Keywords

Nitro Group Nitro Compound Methyl Acetate Electron Ionization Mass Spectrum Ortho Hydrogen 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

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    Nibbering, N. M. M; de Boer, T. J. Mass Spectrometry of Aralkyl Compounds with a Functional Group. Part IV. Specific Exchange Between the α- and ortho-Hydrogen Atoms in the Molecular Ion of γ-Phenylpropylbromide. Tetrahedron 1968, 24, 1427–1434.CrossRefGoogle Scholar
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    Molenaar-Langeveld, T. A; Nibbering, N. M. M. On the 1,1-Elimination of Nitrous Acid and the Loss of Hydroxyl from the Molecular Ion of the Methyl Ester of γ-Nitrobutyric Acid. Org. Mass Spectrom. 1974, 9, 257–263.CrossRefGoogle Scholar
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    Woodward, R. B; Hoffmann, R. The Conservation of Orbital Symmetry Verlag Chemie: Weinheim, 1970.Google Scholar

Copyright information

© American Society for Mass Spectrometry 2004

Authors and Affiliations

  1. 1.Laser Center and Chemistry DepartmentVrije UniversityAmsterdamThe Netherlands

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