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Preparation and stereochemistry of 3‐phenacylidenephthalimidines
Author(s) -
Howe Robert K.
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220118
Subject(s) - chemistry , phthalimide , homonuclear molecule , acetic acid , solvent , diastereomer , organic chemistry , stereochemistry , molecule
Yields of 3‐phenacylidenephthalimidines are maximized and yields of phthalimide byproducts are minimized by use of acetic acid as the solvent in reactions of amines with 3‐phenacylidenephthalides. The 3‐phenacylidenephthalimidines are formed as E, Z mixtures, in which the E isomers predominate. A homonuclear NOE nmr experiment was employed to determined product stereochemistry.