Reaction of ferrocenecarbothioamide and N-(ethoxycarbonyl)ferrocenecarbothioamide with alkyl halides

Reaction of ferrocenecarbothioamide and N-(ethoxycarbonyl)ferrocenecarbothioamide with alkyl (mainly benzyl) halides in the presence of K2CO3 has been studied. The former compound yielded cyanoferrocene in high yield whereas the latter was transformed into the corresponding thioimidates as a result of S-alkylation and deprotonation. The molecular structure of S-p-nitrobenzyl-N-(ethoxycarbonyl)-ferrocenethioimidate was determined by single-crystal X-ray analysis and revealed the E configuration. The plausible reaction mechanism is discussed.