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.
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Nibbering, N. M. M; de Boer, T. J; Hofman, H. J. Mass Spectrometry of Nitro Compounds. Part I. Mass spectra of α-, β-, and γ-Deuterated 1-Nitropropane. Rec. Trav. Chim. Pays-Bas 1965, 84, 481–487.
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.
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.
Woodward, R. B; Hoffmann, R. The Conservation of Orbital Symmetry Verlag Chemie: Weinheim, 1970.
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Published online June 9, 2004
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Nibbering, N.M.M. The McLafferty rearrangement: A personal recollection. J Am Soc Mass Spectrom 15, 956–958 (2004). https://doi.org/10.1016/j.jasms.2004.04.025
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DOI: https://doi.org/10.1016/j.jasms.2004.04.025