- 作者: 林振東 ; 黃百平 ; 周德璋
- 作者服務機構: 東海大學化學系
- 中文摘要: The title hydrocarbon 3, a C/sub 14/H/sub 14/ tetracyclic tetraene of C/sub 2v/-symmetry, was synthesized by new routes starting from 1,8,9,10-tetrachloro-11,11- dimethoxytricyclo [ 6.2.1.0/sup 2,7/ ] undeca-3,5,9-triene(1). The Diels-Alder cycloaddition of 1 with 2-chloroacrylyl chloride, a ketene equivalent, followed by subsequent reduction, dechlorination and deacetalization afforded the ketol 12 as a key intermediate. Elaboration of target compound 3 was carried out by either the method of ring enlargement of 12 or (better) the route of Diels-Alder reaction of decarbonylated 12 with trans-1,2- bis(phenylsulfonyl)ethene, an acetylene equivalent, to give trienol 17, followed by dehydration. Upon irradiation, 3 underwent intercyclic [ 2+2 ] -addition to caged hexacyclic diene. At 120.degree.C, 3 decomposed into barrelene and benzene quantitatively.
- 英文摘要: --
- 中文關鍵字: Synthesis; Tetracyclic Tetraene; Photoaddition; Diels-Alder Reaction; Trienol
- 英文關鍵字: 合成;四環四烯類;光加成反應;Diels-Alder反應;三烯醇