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The [1,2]-thio-Wittig rearrangement: evidence for a radical mechanism and its suppression

The [1,2]-thio-Wittig rearrangement: evidence for a radical mechanism and its suppression
The [1,2]-thio-Wittig rearrangement: evidence for a radical mechanism and its suppression
The lithium enolate formed from methyl S-trityl mercaptoacetate can be C-alkylated in high yield at or below -40 degrees C, but at higher temperatures the [1,2]-thio-Wittig rearrangement of the enolate is the predominant process; ESR evidence indicates that this rearrangement occurs by a radical mechanism.
wittig rearrangement, ab-initio, -wittig rearrangements, pantocin b, -wittig, lithium, ethers, anion, acid, isomerization
0040-4039
7939-7942
Bertolli, Paola
08eeb184-4bed-4168-96ec-82123444b575
Farley, Robert D.
45a7565d-1ee8-465e-90d1-c0b83cb3a9c1
Fletcher, Matthew D.
87623f57-d057-4cb8-be14-42273ab81069
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Paradela, Cristina
1b9dc276-25e0-4b9f-9f15-d4bf6be7a339
von Vacano, Bernhard
1dd6396b-bc87-452d-bb47-2f106cc8af41
Bertolli, Paola
08eeb184-4bed-4168-96ec-82123444b575
Farley, Robert D.
45a7565d-1ee8-465e-90d1-c0b83cb3a9c1
Fletcher, Matthew D.
87623f57-d057-4cb8-be14-42273ab81069
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Paradela, Cristina
1b9dc276-25e0-4b9f-9f15-d4bf6be7a339
von Vacano, Bernhard
1dd6396b-bc87-452d-bb47-2f106cc8af41

Bertolli, Paola, Farley, Robert D., Fletcher, Matthew D., Horton, Peter N., Hursthouse, Michael B., Paradela, Cristina and von Vacano, Bernhard (2006) The [1,2]-thio-Wittig rearrangement: evidence for a radical mechanism and its suppression. Tetrahedron Letters, 47 (45), 7939-7942. (doi:10.1016/j.tetlet.2006.08.140).

Record type: Article

Abstract

The lithium enolate formed from methyl S-trityl mercaptoacetate can be C-alkylated in high yield at or below -40 degrees C, but at higher temperatures the [1,2]-thio-Wittig rearrangement of the enolate is the predominant process; ESR evidence indicates that this rearrangement occurs by a radical mechanism.

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More information

Published date: 2006
Keywords: wittig rearrangement, ab-initio, -wittig rearrangements, pantocin b, -wittig, lithium, ethers, anion, acid, isomerization

Identifiers

Local EPrints ID: 44382
URI: https://eprints.soton.ac.uk/id/eprint/44382
ISSN: 0040-4039
PURE UUID: fc9c929f-366e-4f24-a647-b3d4d3462ba8
ORCID for Peter N. Horton: ORCID iD orcid.org/0000-0001-8886-2016

Catalogue record

Date deposited: 28 Feb 2007
Last modified: 14 Mar 2019 01:47

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Contributors

Author: Paola Bertolli
Author: Robert D. Farley
Author: Matthew D. Fletcher
Author: Peter N. Horton ORCID iD
Author: Cristina Paradela
Author: Bernhard von Vacano

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