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Utilization Of Thiocarbonyl Transfer Reagents. Preparation Of Thioamides, Mercapto Esters, And Thiapyran Derivatives

David N. Harpp, J. Gavin MacDonald, Charles Larsen

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The reaction of 1,1′-thiocarbonyldiimidazole and 1,1′-thiocarbonylbis(1,2,4-triazole) with several aldonitrones has been found to afford thioamides in good yield. Several 1,1′-thiocarbonylbisazoles, which have been shown to undergo Diels–Alder additions with dienes to give cyclic and bicyclic adducts, can be further converted to mercapto esters, thiapyrans, and thiapyranones in good yield.