PRODUCT STRUCTURE AS A FUNCTION OF REACTION CONDITIONS IN THE REACTION OF FORMALDEHYDE WITH AN ALPHA-MERCAPTO AMIDE

Treatment of mercapto amide (3) with formaldehyde and acid or base res ults in products whose structures are a function of the reaction condi tions. Lactone (8), hemithioacetal (9), and dimer (7) were formed in g ood yields under acidic reaction conditions. In addition, dienenone (1 0) was produced from the treatment of (9) with strongly coordinating L ewis acids. Treatment of (9) with NH3/MeOH gave the desired thiazolidi none (1) in moderate yield.