Condensation reactions involving the α-methylene group in series of 5-alkylpyrrolidine-2-thiones and 5-alkyl-1-acetyl-2-pyrrolidones
It is shown that 1-substituted and N-unsubstituted 5-R-pyrrolidine-2-thiones, in contrast to their oxygen analogs, undergo methylenethioalkylation and the Mannich and Michael reactions at the 3 position of the ring; this is due to their higher CH acidity. The results of quantum-chemical calculations (by the MO LCAO method within the CNDO/2 approximation) confirm the similar reactivities of pyrrolidine-2-thiones and 1-acetyl-substituted 2-pyrrolidones.
KeywordsOxygen Organic Chemistry Acidity Condensation Reaction Similar Reactivity
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