Reactions of Triphenyltin Hydride with Certain Acid Chlorides and Carboxylic Acids

Chemistry of Acyl Radicals

“…The stannane-mediated reduction of acyl chlorides to aldehydes via acyl radicals is plagued by the formation of byproducts, typically esters, which may even become the major products depending on the conditions. Thus, early workers studying the reduction of benzoyl chloride noted the formation of benzyl benzoate and, under certain conditions, its exclusive nature. − There was much discussion about the mechanism of ester formation 109-114 until Ingold and co-workers convincingly demonstrated it to involve over-reduction of the aldehyde by a polar mechanism and reaction of a stannyl alkoxide with the acyl chloride. , In light of these complications, as is evident from sections VII and VIII, studies on the use of acyl radicals generated from acyl chlorides in synthesis are quite limited.…”

Reaction of ferrocenecarboxylic acid with N,N′-disubstituted carbodiimides: synthesis, spectroscopic and X-ray crystallographic analysis of N,N′-disubstituted N-ferrocenoylureas and identification of a one-pot coupling reagent for the formation of ferrocenecarboxamides in a non-aqueous solvent

“…The clear brown solution was concentrated to 4 ml and separated by column chromatography (CC) with silica gel as the stationary phase and a mixture of acetone and dichloromethane as the eluent. The first coloured fraction was 8 [16] (yields see Table 2), the second was the ferrocenoylurea. The solvent was removed by vacuum and the resulting solid was kept at 0.1 mbar to remove trace amounts of carbodiimide.…”

Ferrocenecarboxylic anhydride: identification of a new polymorph

“…Reference samples were further prepared by the reaction of FcCOCl with water in the presence of pyridine. Kupchik & Kiesel (1966) reported the unexpected formation of (1) during the reaction of FcCOCl with tributyltin hydride, which was supposed to deliver the corresponding ferrocenecarbaldehyde or ester. A reference sample was also prepared, that time by reacting FcCOCl with FcCO 2 Na.…”