| Cope reaction | |
|---|---|
| Named after | Arthur C. Cope |
| Reaction type | Elimination reaction |
| Identifiers | |
| Organic Chemistry Portal | cope-elimination |
| RSC ontology ID | RXNO:0000539 |
The Cope reaction or Cope elimination, developed by Arthur C. Cope, is the elimination reaction of an N-oxide to an alkene and a hydroxylamine.[1][2][3][4]
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:[5]
- ^ Cope, Arthur C.; Foster, Theodore T.; Towle, Philip H. (1949). "Thermal Decomposition of Amine Oxides to Olefins and Dialkylhydroxylamines". Journal of the American Chemical Society. 71 (12): 3932–3935. doi:10.1021/ja01180a014.
- ^ Cope, Arthur C.; Towle, Philip H. (1949). "Rearrangement of Allyldialkylamine Oxides and Benzyldimethylamine Oxide". Journal of the American Chemical Society. 71 (10): 3423–3428. doi:10.1021/ja01178a048.
- ^ Cope, Arthur C.; Pike, Roscoe A.; Spencer, Claude F. (1953). "Cyclic Polyolefins. XXVII. cis- and trans-Cycloöctene from N,N-Dimethylcycloöctylamine". Journal of the American Chemical Society. 75 (13): 3212–3215. doi:10.1021/ja01109a049.
- ^ Peter C. Astles; Simon V. Mortlock; Eric J. Thomas (1991). "The Cope Elimination, Sulfoxide Elimination and Related Thermal Reactions". Comprehensive Organic Synthesis. Vol. 6. pp. 1011–1039. doi:10.1016/B978-0-08-052349-1.00178-5. ISBN 978-0-08-052349-1.
- ^ Cope, Arthur C.; Ciganek, Engelbert (1963). "Methylenecyclohexane and N,N-Dimethylhydroxylamine Hydrochloride". Organic Syntheses. 4: 612. doi:10.15227/orgsyn.039.0040.