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Pummerer reaction intermediate as an initiating function for cationic olefin cyclization
Authors:Y Tamura  H Maeda  S Akai  K Ishiyama  H Ishibashi
Institution:Faculty of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, Japan
Abstract:Treatment of N-(2-methyl-2-propenyl)-N-methyl-α-(methylsulfinyl)acetamide (6a) with trifluoroacetic anhydride caused the cationic olefin cyclization through a Pummerer reaction intermediate to give the six-membered lactams 7 and 8. Similar reaction converted N-2-butenyl-N-methyl-a-(methylsulfinyl)acetamide (6b) to the five-membered lactam 9, and N-2-propenyl-N-methyl-α-(methylsulfinyl)- acetamide (6c) to the five-membered lactams 11 and 12.
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