Cope Elimination Reaction

The sterically demanding amine oxide function reacts preferentially with the more easily accessible hydrogens, and often gives good selectivity favoring the less-substituted alkene. Thus, for simple alkenes, the reaction follows the Hofmann Rule.

The Cope Elimination is a syn periplanar elimination in which six electrons move in a five-membered ring according to a concerted, thermally-induced mechanism to yield an alkene and a hydroxylamine.

The sterically demanding amine oxide function reacts preferentially with the more easily accessible hydrogens, and often gives good selectivity favoring the less-substituted alkene. Thus, for simple alkenes, the reaction follows the Hofmann Rule.

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References :

[1]O'Neil I A, Ramos V E, Ellis G L, et al. The diastereoselective synthesis of functionalised isoxazolidines using a Cope elimination/intramolecular nitrone cycloaddition strategy[J]. Tetrahedron letters, 2004, 45(18): 3659-3661.

[2]Remen L, Vasella A. Conformationally Biased Mimics of Mannopyranosylamines: Inhibitors of β‐Mannosidases?[J]. Helvetica chimica acta, 2002, 85(4): 1118-1127.

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