The bromination of β-angelica lactone revisited: Synthesis of new 3-bromo-5-methylene- and 3-bromo-5-methyl-2(5H)-furanones.
✍ Scribed by Cristina Ochoa de Echagüen; Rosa M. Ortuño
- Book ID
- 108372254
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 368 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4020
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📜 SIMILAR VOLUMES
## Abstract Highly optically active 4‐substituted‐2(5__H__)‐furanones 6a‐6j were obtained in good yields with __de__⩾98% by the tandem Michael addition/elimination reaction of chiral 3‐bromo‐2(5__H__)‐furanone (4a), which was conveniently prepared starting from 2‐furaldehyde under mild conditions.
Treatment of methyl 2,3-pentadienoate, 3, with bromine in carbon tetrachloride affords a complex mixture. whose main products are methyl (g)-and fZ)-3,4-dibromo-2-pentenoate, 9 and 10, and I-bromo-5methyl-5E-furan-2zone, 4. The mechanism of formation of these and other minor compounds is discussed.