Editing Cope reaction (section)

{{Short description|Reaction of N-oxide to alkene and hydroxylamine}}
{{distinguish|Cope rearrangement}}
{{Reactionbox
| Name = Cope reaction
| Type = Elimination reaction
| NamedAfter = [[Arthur C. Cope]]
| Section3 = {{Reactionbox Identifiers
   | OrganicChemistryNamed = cope-elimination
   | RSC_ontology_id = 0000539
 }}
}}
The '''Cope reaction''' or '''Cope elimination''', developed by [[Arthur C. Cope]], is the [[elimination reaction]] of an [[Amine oxide|N-oxide]] to an [[alkene]] and a [[hydroxylamine]].<ref>{{cite journal |last1=Cope |first1=Arthur C. |last2=Foster |first2=Theodore T. |last3=Towle |first3=Philip H. |author-link1=Arthur C. Cope |title=Thermal Decomposition of Amine Oxides to Olefins and Dialkylhydroxylamines |journal=[[Journal of the American Chemical Society]] |date=1949 |volume=71 |issue=12 |pages=3932–3935 |doi=10.1021/ja01180a014}}</ref><ref>{{cite journal |last1=Cope |first1=Arthur C. |last2=Towle |first2=Philip H. |author-link1=Arthur C. Cope |title=Rearrangement of Allyldialkylamine Oxides and Benzyldimethylamine Oxide |journal=[[Journal of the American Chemical Society]] |date=1949 |volume=71 |issue=10 |pages=3423–3428 |doi=10.1021/ja01178a048}}</ref><ref>{{cite journal |last1=Cope |first1=Arthur C. |last2=Pike |first2=Roscoe A. |last3=Spencer |first3=Claude F. |author-link1=Arthur C. Cope |title=Cyclic Polyolefins. XXVII. cis- and trans-Cycloöctene from N,N-Dimethylcycloöctylamine |journal=[[Journal of the American Chemical Society]] |date=1953 |volume=75 |issue=13 |pages=3212–3215 |doi=10.1021/ja01109a049}}</ref><ref>{{cite encyclopedia|volume=6|year=1991|pages=1011–1039|encyclopedia=Comprehensive Organic Synthesis|title=The Cope Elimination, Sulfoxide Elimination and Related Thermal Reactions |author=Peter C. Astles |author2=Simon V. Mortlock |author3=Eric J. Thomas|doi=10.1016/B978-0-08-052349-1.00178-5|isbn=978-0-08-052349-1}}</ref>[[Image:CopeReaction.png|554px|Cope reaction|center]]Typically, the amine oxide is prepared from the corresponding [[amine]] with a [[peroxy acid]] or comparable [[oxidant]].  The actual elimination requires just heat.  
Illustrative is a synthesis of [[methylenecyclohexane]]:<ref>{{cite journal |last1=Cope |first1=Arthur C. |author-link1=Arthur C. Cope |last2=Ciganek |first2=Engelbert |date=1963 |title=Methylenecyclohexane and N,N-Dimethylhydroxylamine Hydrochloride |journal=[[Organic Syntheses]] |volume=4 |page=612 |doi=10.15227/orgsyn.039.0040}}</ref>
[[File:MethyleneCyclohexaneByCopeReaction.svg|center|389x389px|synthesis of methylenecyclohexane]]