The [1,2]-thio-Wittig rearrangement: evidence for a radical mechanism and its suppression
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).
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Original Publication URL: http://dx.doi.org/10.1016/j.tetlet.2006.08.140
Description/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.
| Item Type: | Article |
|---|---|
| ISSNs: | 0040-4039 (print) |
| Related URLs: | |
| Keywords: | wittig rearrangement, ab-initio, -wittig rearrangements, pantocin b, -wittig, lithium, ethers, anion, acid, isomerization |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 44382 |
| Date Deposited: | 28 Feb 2007 |
| Last Modified: | 01 Jun 2011 06:54 |
| Contributors: | Bertolli, Paola (Author) Farley, Robert D. (Author) Fletcher, Matthew D. (Author) Horton, Peter N. (Author) Hursthouse, Michael B. (Author) Paradela, Cristina (Author) von Vacano, Bernhard (Author) |
| Date: | 2006 |
| Status: | Published |
| Contact Email Address: | m.d.fletcher@fish.co.uk |
| URI: | http://eprints.soton.ac.uk/id/eprint/44382 |
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