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Communication | Regular issue | Vol 16, No. 2, 1981, pp.209-214
Published online, 1st January, 1970
DOI: 10.3987/R-1981-02-0209
Reactions of 4-Methylene-2-phenyl-2-oxazolin-5-ones with Sulfer Ylides

Otohiko Tsuge,* Michihiko Noguchi, and Hiroyuki Moriyama

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan


The reaction of 2-phenyl-4-phenylmethylene-2-oxazolin-5-one with dimethyloxosulfonium methylide proceeded via a nucleophilic attack of the methylide on the carbonyl carbon in the oxazolinone with concurrent ring opening to give 1:1 adduct, dimethyloxosulfonium (2-benzamido)cinnamoylmethylide. On the other hand, dimethylsulfonium phenacylide reacted with 4-phenylmethylene-, 4-(p-acetoxyphenyl)methylene-, 4-styrylmethylene-, 4-(2-furyl)methylene-, 4-[3-(1-acetylindolyl)]methylene-, or 4-dimethylmethylene-2-phenyl-2-oxazolin-5-one to give two stereoisomeric spirocyclopropanes and/or γ-pyrone derivatives respectively, whose yields were dependent on the reaction conditions.