55834-30-5Relevant academic research and scientific papers
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.
VICINAL ALKYLATION OF OLEFINS, REGIO- AND STEREOSELECTIVE ADDITION OF M + CN> UNITS TO CYCLOPENTADIENE.
Michel, P.,O'Donnell, M.,Biname, R.,Hesbain-Frisque, A.M.,Ghosez, L.,et al.
, p. 2577 - 2580 (2007/10/02)
Adducts of alkyl(phenylthio)ketenes to cyclopentadiene are cleaved with KOH-t-BuOK with retention of configuration at three centers.This observation broadens the synthetic potential of the method of vicinal alkylation of olefins.This method has been used for the vicinal addition of m + Cn> units to cyclopentadiene.
