A synthetic route to the morphan ring system by skeletal transformation of norbornadiene.
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概要
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The morphan skeleton was prepared from 2-phenylsulfonyl-2-azabicyclo[3.2.1]oct-6-ene (<B>2</B>), derived from norbornadiene, through the addition of dichlorocarbene to the monoene <B>2</B> and the subsequent thermal isomerization of the adduct obtained. The isomerization products, 2-phenylsulfonyl-6,7-dichloro-2-azabicyclo[3.3.1]non-7-ene and 2-phenylsulfonyl-7,8-dichloro-2-azabicyclo[3.3.1]non-6-ene, which are mutually convertible in the presence of lithium chloride, were converted into various morphans by reductive dechlorination and alkylation. Furthermore, the 6,7-pyridazino-annelated morphan was synthesized by the cycloaddition of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate to 2-phenylsulfonyl-2-azabicyclo[3.3.1]non-6-ene.
- 公益社団法人 日本化学会の論文
著者
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Inoue Hiroo
Department Of Applied Chemistry College Of Engineering Osaka Prefecture University
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Origuchi Toshiki
Department of Applied Chemistry, College of Engineering, University of Osaka Prefecture
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Umano Katsumi
Department of Applied Chemistry, College of Engineering, University of Osaka Prefecture
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