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[2,3]-Sigmatropic rearrangements of didehydropiperidinium ylids

[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
0040-4020
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
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), 10113-10126. (doi:10.1016/S0040-4020(02)01397-2).

Record type: Article

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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More information

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
ORCID for Ali Tavassoli: ORCID iD orcid.org/0000-0002-7420-5063

Catalogue record

Date deposited: 21 Mar 2007
Last modified: 08 Jan 2022 03:04

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Contributors

Author: J.B. Sweeney
Author: Ali Tavassoli ORCID iD
Author: Neil B. Carter
Author: Jerome F. Hayes

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