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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== [[Orange Book]] Entry == | == [[Orange Book]] Entry == | ||
{{orange| | |||
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. | 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. | ||
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== [[Gold Book]] Entry == | == [[Gold Book]] Entry == | ||
{{gold| | |||
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. | 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. | ||
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== External Links == | == External Links == | ||
*[[Wikipedia:McLafferty rearrangement]] | |||
*[http://www.iupac.org/goldbook/M03772.pdf IUPAC Gold Book Entry (PDF)] | *[http://www.iupac.org/goldbook/M03772.pdf IUPAC Gold Book Entry (PDF)] | ||
*[http://themerckindex.cambridgesoft.com/TheMerckIndex/NameReactions/onr240.htm CambridgeSoft Link] | *[http://themerckindex.cambridgesoft.com/TheMerckIndex/NameReactions/onr240.htm CambridgeSoft Link] | ||
*[http://masspec.scripps.edu/information/history/names/detail.html?id=12 Fred McLafferty Biography (Scripps)] | *[http://masspec.scripps.edu/information/history/names/detail.html?id=12 Fred McLafferty Biography (Scripps)] | ||
[[Category:Reactions]] | [[Category:Reactions]] | ||
Revision as of 19:01, 10 July 2009
Obsolete Template
Orange Book Entry
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 |
|---|
|
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 Entry
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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|
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. |
| IUPAC Gold Book |
| Index of Gold Book Terms |
