THE MEYER-SCHUSTER REARRANGEMENT AND HYDROHALIDE ADDITION OF 3-ALKYNYL-3-HYDROXY-1H-ISOINDOL-1-ONES

Treatment of N-methyl and N-phenylphthalimide with appropiate lithium acetylides in tetrahydrofuran obtained the acetylenic alcohols 2a through 2h. These compounds, when subjected to mildly acidic hydrolysis conditions in aqueous organic solvents, underwent Meyer-Schuster rearrangement to yield the alpha,beta-unsaturated carbonyl compounds 4a through 4h which were determined to have the E configuration. The phenyl ethynyl analogs of series 4 underwent hydrohalide addition when treated with hydrogen halides in water solution.