[2,3]-Sigmatropic rearrangements of didehydropiperidinium ylids
[2,3]-Sigmatropic rearrangements of didehydropiperidinium ylids
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 transformation 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.
ammonium ylids [2, 3]-rearrangement vinyl proline acids analogs
10113-10126
Sweeney, J.B.
c074346d-11b2-4b8b-a9fa-63435c1f9594
Tavassoli, Ali
d561cf8f-2669-46b5-b6e1-2016c85d63b2
Carter, Neil B.
934871d4-4187-4d3c-a0c9-0ccba8f5e759
Hayes, Jerome F.
c8a8729f-4fda-43ed-ada7-e50bb50d8eca
2002
Sweeney, J.B.
c074346d-11b2-4b8b-a9fa-63435c1f9594
Tavassoli, Ali
d561cf8f-2669-46b5-b6e1-2016c85d63b2
Carter, Neil B.
934871d4-4187-4d3c-a0c9-0ccba8f5e759
Hayes, Jerome F.
c8a8729f-4fda-43ed-ada7-e50bb50d8eca
Sweeney, J.B., Tavassoli, Ali, Carter, Neil B. and Hayes, Jerome F.
(2002)
[2,3]-Sigmatropic rearrangements of didehydropiperidinium ylids.
Tetrahedron, 58 (51), .
(doi:10.1016/S0040-4020(02)01397-2).
Abstract
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 transformation 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.
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Published date: 2002
Keywords:
ammonium ylids [2, 3]-rearrangement vinyl proline acids analogs
Identifiers
Local EPrints ID: 45314
URI: http://eprints.soton.ac.uk/id/eprint/45314
ISSN: 0040-4020
PURE UUID: 8c7b391a-0a67-48d2-a0a1-25e56b510011
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Date deposited: 21 Mar 2007
Last modified: 16 Mar 2024 03:51
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Author:
J.B. Sweeney
Author:
Neil B. Carter
Author:
Jerome F. Hayes
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