Synthesis and thermal rearrangement of 2-allyl substituted 2H-pyrrole derivatives
β Scribed by Albert Padwa; Yashwant Kulkarni
- Publisher
- Elsevier Science
- Year
- 1979
- Tongue
- French
- Weight
- 188 KB
- Volume
- 20
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
Substituted pyrrole derivatives are prepared by treatment of 2,3-dihydrofuran derivatives with trifluoroacetic acid. These in turn are obtained by Michael addition of carbon nucleophiles of the b-dicarbonyl type to N-(4-toluenesulfonyl)-N-(tertbutyloxycarbonyl)-dehydroalanine methyl ester.
## Abstract The Claisen rearrangement of Oβallyl substituted isotetronic acids of type (I), (III), or (V) is described.
O-2-(Acyl)vinylketoximes (freshly prepared from ketoximes and acylacetylenes in the presence of Ph 3 P as catalyst in up to 83% yields) rearrange upon heating (125-150 Β°C) to give 2-or 3-acylpyrroles, wherein the positions of the acyl substituents do not correspond to known O-vinyloxime rearrangemen