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Communication | Special issue | Vol 13, No. 1, 1979, pp.293-296
Published online, 1st January, 1970
DOI: 10.3987/S-1979-01-0293
Studies on Hetero-cage Compounds. 9. Synthesis and Chemical Reactivity of 8-Thiabicyclo [3.2.1] octan-3-one System in Comparison with 9-Thiabicyclo [3.3.1] nonan-3-one System

Tadashi Sasaki,* Shoji Eguchi, and Tadashi Hioki

*Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan


Treatment of cyclohepta-2,6-dienone (5) with Na2S in H2O-MeOH afforded 8- thiabicyclo[3.2.1]octan-3-one (6) in 38% yield. Oxidation of 6 with m-CPBA gave sulfone 8 and reduction of 6 with NaBH4 gave endo- (9) and exo-alcohols (10) in 33:67 ratio. The carbene 12 generated via Na salt of tosylhydrazone 11a yielded only 8-thiabicyclo[3.2.1]oct-2-ene (13), a H migration product.