α-Ketodicarbonsäurechlorid-imidchloride in der Heterocyclensynthese, III. Über eine neuartige Wittig-Smiles-Reaktion
✍ Scribed by Capuano, Lilly ;Bettinger, Arthur ;Engel, Michael ;Pfordt, Martin ;Huch, Volker
- Publisher
- John Wiley and Sons
- Year
- 1988
- Tongue
- English
- Weight
- 251 KB
- Volume
- 1988
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
a-Ketodicarboxylic Acid Chloride h i d e Chlorides in the Synthesis of Heterocycles, 111'). -A Novel Wittig-Smiles Reaction N-Cyclohexyl-2.2-dimethyl-3-oxosuocinyl chloride imide chloride (1) reacts with methylenetriphenylphosphoranes &ording 3-henzy l idene-1 -cyclohexyl-4.4-dimethyl-2,5-pyrrolidinediones 10 through a novel Wittig-Smiles mechanism. The structure of compound 1Oa is confirmed by X-ray diffraction analysis. When thc ylidc carbon carries a methyl or phenyl substituent, the Wittig-Smiles reaction fails, and cyclization results merely in the formation of 1 -cyclohexyl-4,~dimethyl-~3,5-pyrrolidione (4).