✦ LIBER ✦
Unusual (1,2) wittig rearrangement of a carbanion generated in neutral aqueous medium by photodecarboxylation of a phenoxyacetic acid analogue
✍ Scribed by Miguel A. Miranda; Francisco Bosca; Frnaklin Vargas; Nieves Canudas
- Book ID
- 103993977
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- English
- Weight
- 263 KB
- Volume
- 78
- Category
- Article
- ISSN
- 1010-6030
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✦ Synopsis
An unexpected
(1,2) Wittig rearrangement occurs upon photodecarboxylation of fenofibric acid in neutral aqueous medium, by contrast with the usual experimental conditions employed in this type of rearrangement (alkyllithiums in dry THF or ethyl ether). Solvent effects suggest a mechanism invohring cyclization of the decarboxylated carbanion to a resonance-stabilized oxacyclopropyl intermediate, rather than the generally operating radical cleavage-recombination pathway.