McLafferty rearrangement: Difference between revisions
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A dissociation reaction triggered by transfer of a hydrogen atom via a 6-member transition state to the formal radical/charge site from a carbon atom four atoms removed from the charge/radical site (the ?????????????-carbon); subsequent rearrangement of electron density leads to expulsion of an olefin molecule. This term was originally applied to ketone ions where the charge/radical site is the carbonyl oxygen, but it is now more widely applied. | A dissociation reaction triggered by transfer of a hydrogen atom via a 6-member transition state to the formal radical/charge site from a carbon atom four atoms removed from the charge/radical site (the ?????????????-carbon); subsequent rearrangement of electron density leads to expulsion of an olefin molecule. This term was originally applied to ketone ions where the charge/radical site is the carbonyl oxygen, but it is now more widely applied. | ||
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A rearrangement reaction involving transfer of a hydrogen atom via a 6-member transition state to the formal radical/charge site from a carbon atom four atoms distant from the charge/radical site (the ?-carbon); subsequent rearrangement of electron density can lead to expulsion of an olefin molecule. | |||
Note: Originally applied to ketone ions where the charge/radical site is the carbonyl oxygen, but it is now more widely applied. | |||
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#[[Orange Book]] | |||
#[[Gold Book]] | |||
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Orange Book
| ORANGE BOOK DEFINITION
IUPAC. Analytical Division. Compendium of Analytical Nomenclature (the Orange Book). Definitive Rules, 1979 (see also Orange Book 2023) |
| McLafferty rearrangement |
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This is an example of a rearrangement reaction and is defined as β - cleavage with concomitant specific transfer of a γ - hydrogen atom in a six-membered transition state in mono-unsaturated systems, irrespective of whether the rearrangement is formulated by a radical or by an ionic mechanism and irrespective of with which fragment the charge stays. |
| IUPAC 1997 Orange Book Chapter 12 |
| Index of Orange Book Terms |
Gold Book
| GOLD BOOK DEFINITION
IUPAC. Compendium of Chemical Terminology, 2nd ed. (the Gold Book). Compiled by A. D. McNaught and A.Wilkinson. Blackwell Scientific Publications, Oxford (1997). |
| McLafferty rearrangement |
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http://goldbook.iupac.org/M03772.html β-Cleavage with concomitant specific transfer of a γ-hydrogen atom in a six-membered transition state in mono-unsaturated systems, irrespective of whether the rearrangement is formulated by a radical or an ionic mechanism, and irrespective of the position of the charge. Source: Orange Book p. 207 |
| IUPAC Gold Book |
| Index of Gold Book Terms |
External links
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This term has a corresponding Wikipedia article: Wikidata page for McLafferty rearrangement |
