Reactions of Ketenes with Sulfilimines. Synthetic Routes to Oxazolinones and Indolinones

Article abstract of DOI:10.1021/jo00213a005

The reactions of diphenylketene and tert-butylcyanoketene with several sulfilimines were investigated. 5,5-Diphenyl-2-oxazolin-4-ones were produced from N-acylsulfilimines and diphenylketene while a 2-indolinone was obtained from N-arylsulfilimine and the same ketene. tert-Butylcyanoketene afforded either simple substituted or ortho-rearranged amides when S,S-dimethylsulfilimines were used as substrates.The structure of 2,5,5-triphenyloxazolidin-4-one (7b) was confirmed by single-crystal X-ray examination.Possible mechanistic pathways which account for all observed products are discussed.