Reactivity of dimethyl N-(ethoxycarbonylmethyl)iminodithiocarbonate with carbonyl compounds in basic medium

Abstract

The reactivity of dimethyl N-(ethoxycarbonylmethyl)iminodithiocarbonate with aromatic aldehydes and reactive ketones has been studied. Ethyl 3-aryl-2-(methylthiocarbonylamino)acrylates (1) are obtained with aromatic aldehydes by ring-opening isomerization of the intermediate 5-aryl-4ethoxycarbonyl-2-methylthio-4,5-dihydro-1,3-oxazoles (2). With ketones it has been shown that the cycloalkanones give rise to the corresponding alkylidene derivatives by a reaction path identical with that of aromatic aldehydes, whereas hexafluoropropanone and 1,1,1-trifluoropropanone display duality in acting as both acylating reagents and carbonyl compounds.