76822-08-7Relevant articles and documents
Rhodium-Catalyzed Rearrangement of α-Diazo Thiol Esters to Thio-Substituted Ketenes. Application in the Synthesis of Cyclobutanones, Cyclobutenones, and β-Lactams
Lawlor, Michael D.,Lee, Thomas W.,Danheiser, Rick L.
, p. 4375 - 4384 (2007/10/03)
Exposure of α-diazo thiol esters (1) to the action of catalytic rhodium(II) acetate leads to a remarkably facile "thia-Wolff rearrangement", producing thio-substituted ketenes which combine with a variety of ketenophiles to provide access to α-thiocyclobutanones, cyclobutenones, and β-lactams. Reductive desulfurization of these cycloadducts takes place under mild conditions and in excellent yield, and this sequence thus represents a useful new alternative to the existing dichloroketene-based methodology for the synthesis of four-membered carbocycles and heterocycles.