86002-02-0Relevant articles and documents
Reactions of organoboranes with carbanions bearing three potential leaving groups: unusual processes, products and mechanisms
Saleh, Basil A.,Smith, Keith,Elliott, Mark C.,Jones, D. Heulyn,Kariuki, Benson M.,El Hiti, Gamal A.
, p. 6914 - 6928 (2016/10/14)
Known reagents that transfer three alkyl groups of a trialkylborane intramolecularly to a single carbon atom lack features to influence stereochemistry. We have investigated four reagents of type LiCCl2X, where X might be amenable to variation. All behaved differently. With X=OR (R=cyclohexyl, menthyl), the reagent decomposed, leading to only low yields of triple migration products. With X=S(O)Ph, a single migration occurred, followed by isomerisation to boron enolate-like species that hydrolysed to α-chloroalkyl phenyl sulfoxides or reacted with aldehydes to aldol-like products. With X=SO2Ph, the major product was the corresponding α,α-dichloroalkyl phenyl sulfone, apparently formed through a redox reaction. With X=S(O)(NMe)Ph, products of three intramolecular alkyl migrations were obtained with unhindered trialkylboranes. Attempts have been made to gain understanding of the sulfoxide process by investigating proportions of aldol-like products, using X-ray crystallography and ab initio calculations.
DICHLOROMETHYL PHENYL SULFOXIDE: SYNTHETIC APPLICATIONS
Reutrakul, Vichai,Herunsalee, Kitivit
, p. 527 - 530 (2007/10/02)
Lithio dichloromethyl phenylsulfoxide reacts with aldehydes and alkyl halides to give the corresponding addition and alkylated products respectively.Pyrolysis of these compounds result in the formation of dichloroketones and terminal vinyl dichlorides.
