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α‐Ketodicarbonsäurechlorid‐imidchloride in der Heterocyclensynthese, III. Über eine neuartige Wittig‐Smiles‐Reaktion
Author(s) -
Capuano Lilly,
Bettinger Arthur,
Engel Michael,
Pfordt Martin,
Huch Volker
Publication year - 1988
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198819880918
Subject(s) - wittig reaction , chemistry , substituent , ylide , imide , chloride , smiles rearrangement , medicinal chemistry , organic chemistry
α‐Ketodicarboxylic Acid Chloride Imide Chlorides in the Synthesis of Heterocycles, III. – A Novel Wittig‐Smiles Reaction N ‐Cyclohexyl‐2,2‐dimethyl‐3‐oxosuccinyl chloride imide chloride ( 1 ) reacts with methylenetriphenylphosphoranes affording 3‐benzylidene‐1‐cyclohexyl‐4,4‐dimethyl‐2,5‐pyrrolidinediones 10 through a novel Wittig‐Smiles mechanism. The structure of compound 10a is confirmed by X‐ray diffraction analysis. When the ylide carbon carries a methyl or phenyl substituent, the Wittig‐Smiles reaction fails, and cyclization results merely in the formation of 1‐cyclohexyl‐4,4‐dimethyl‐2,3,5‐pyrrolidinetrione ( 4 ).