Harrington Laura E, Britten James F, McGlinchey Michael J
Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ontario, Canada L8S 4M1.
Org Lett. 2004 Mar 4;6(5):787-90. doi: 10.1021/ol049967o.
The attempted Diels-Alder reaction between 9-phenylethynylfluorene and tetracyclone yields instead three products resulting from the dimerization of the isomeric allene. The major product is 8,16-diphenyl-diindeno[1,2,3-de:1',2',3'-mn]naphthacene, in which each terminal ring is derived from a fluorenyl unit; aerial oxidation then yields a peroxide. A dihydronaphthacene bearing fluorenyl moieties spiro-bonded at the C(5) and C(11) positions was also identified. The structures of the naphthacenes were elucidated by X-ray crystallography, and a mechanistic rationale is offered. [reaction: see text]
9-苯基乙炔基芴与四并环酮之间尝试进行的狄尔斯-阿尔德反应，反而生成了三种由异构丙二烯二聚化产生的产物。主要产物是8,16-二苯基-二茚并[1,2,3-de:1',2',3'-mn]并四苯，其中每个末端环都源自芴基单元；空气氧化后会生成过氧化物。还鉴定出了一种在C(5)和C(11)位置通过螺键连接有芴基部分的二氢并四苯。通过X射线晶体学阐明了并四苯的结构，并给出了机理依据。[反应：见正文]
