199917-93-6Relevant articles and documents
Factors affecting the [3,2]-sigmatropic rearrangements of didehydropiperidinium ylids
Hyett, David J.,Sweeney,Tavassoli, Ali,Hayes, Jerome F.
, p. 8283 - 8286 (1997)
The [3,2] sigmatropic rearrangements of cyclic ammonium ylides have been studied with a view to optimizing rearrangement at the expense of elimination.
[2,3]-Sigmatropic rearrangements of didehydropiperidinium ylids
Sweeney,Tavassoli, Ali,Carter, Neil B.,Hayes, Jerome F.
, p. 10113 - 10126 (2007/10/03)
The [2,3]-sigmatropic rearrangements of ammonium ylids derived from 1,2,5,6-tetrahydropyridine have been studied: both rearrangement and elimination processes are observed, with rearrangement favoured when aprotic solvents are used in the reaction. The presence of anion-stabilizing substituents on the nucleophilic carbon atom of the intermediate ylid species involved in the tranformation also engenders rearrangement; when certain aryl substituents or two anion-stabilizing groups are present, elimination is not observed, and electron-donating ylid substituents retard rearrangement whilst enhancing elimination.
Diastereoselective preparation of cis-2-substituted 3-ethenyl prolines via [3,2]-sigmatropic rearrangements of didehydropiperidinium ylids
Hayes,Tavassoli,Sweeney
, p. 1208 - 1209 (2007/10/03)
The [3,2]-sigmatropic rearrangements of N-(methoxycarbonyl)methyl-N-methyl-1,2,3,6-tetrahydropyridinium bromide (1a) has been extrapolated to allow preparation of (±)-cis-2-aryl-3-ethenyl prolines, and certain spiro-prolines.
