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Paper | Regular issue | Vol 85, No. 10, 2012, pp.2491-2503
Published online, 17th August, 2012
DOI: 10.3987/COM-12-12558
SYNTHESIS OF DIhydrodiBENZo[b,f]furo[2,3-d]OXEPINs AND RELATED REACTIONS

Yasunobu Maemura, Yuka Tanoue, and Hiroshi Nishino*

*Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, Kurokami 2-39-1, Chûou-Ku, Kumamoto 860-8555, Japan

Abstract

Nine dihydrodibenzo[b,f]furo[2,3-d]oxepin derivatives were synthesized by the Mn(III)-based oxidative addition of dibenz[b,f]oxepins at C10-C11 with acetic anhydride, acetylacetone, dialkyl malonates, and malonamide. Oxidative ring-expansion of methyl hydrogen thioxanthenylmalonate with manganese(III) acetate did not give the desired dibenzo[b,f]thiepincarboxylate but produced 2-acetoxy-2-(thioxanthen-9-yl)acetate and thioxanthone.