The rearrangement of R,y-unsaturated ketones in acid has considerable potential for the synthesis of unusual bi-and tricyclic ring systems. In most examples described thus far, however, the double bond is present in the relatively strained cyclobutene ring.' We describe here a synthetically useful r
Novel oxidative rearrangement of β,γ-unsaturated ketone hydrazones on iodination in base
✍ Scribed by Michael E. Jung; Gregory L. Hatfield
- Publisher
- Elsevier Science
- Year
- 1982
- Tongue
- French
- Weight
- 176 KB
- Volume
- 23
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Iodlnation of the bzcyclic enone hydrazone 2 zn excess trzethylamine gave, in addition to the expected vinyl iodrde A. the rearranged aromatic product 5.
📜 SIMILAR VOLUMES
The dimers(La & b) of dimethyl-and diethylcyclopentadienone ketals(la & b) undergo a novel 1,3-alkoxy-rearrangement to 4\_(a & b). Mild hydrolysis of 2 or 3 gives the monoketones (?a or b). On strong acid catalysed hydrolysis 2, 5. or 4 afford the cyciopentadienone-dimer(6) In contrast to the notor
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