Abstract
The reaction of 2,3-bis(phenylsulfonyl)-1,3-butadiene with aryl imines affords N-alkyl-3,5-bis(phenylsulfonyl)-1,2,5,6-tetrahydropyridines in high yield. The formation of the rearranged cycloadducts proceeds by a mechanism that involves addition of benzenesulfinate anion onto the terminal π-bond of the activated diene. The resulting carbanion undergoes proton transfer followed by aryl sulfinate ejection to give 1,3-bis(phenylsulfonyl)-1,3-butadiene as a transient intermediate. This reactive diene undergoes a rapid 4+2 cycloaddition followed by a subsequent hydrogen 1,3-shift
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