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Olefins from Thermal Decomposition of N-Sulfoximino-2-oxazolidones.A Novel Synthesis of Bicyclo[3.3.l]non-l-ene Moon-geu Kim and James D. White* Contribution from the Department of Chemistry, Oregon State University, Corvallis, Oregon 97331. Received July 15, I976
Abstract: 3-Amino-2-oxazolidones (7a-g) were prepared stereospecifically by condensation of 2-hydroxyalkylhydrazines (obtained by hydrazinolysis of the corresponding epoxides) with diethyl carbonate in the presence of sodium methoxide or by Namination of a 2-oxazolidone (7a,e,h-j). The appropriate oxazolidone was prepared either by condensation of a 2-hydroxyalkylamine, obtained by ammonolysis of an epoxide, with phosgene (loa) or N,N'-carbonyldiimidazole (lob), or by nitrosation of a P-hydroxycarbohydrazide (13). Oxidation of 3-amino-2-oxazolidones with lead tetraacetate in MezSO gave the 3-sulfoximino derivatives 14a-j. Except for 14h, these sulfoximines underwent smooth pyrolysis a t
