Dimerization of 9-phenylethynylfluorene to Di-indeno-naphthacene and dispiro-[fluorene-dihydronaphthacenefluorene]: An X-ray crystallographic and NMR study

被引：32

作者：

Harrington, LE

Britten, JF

McGlinchey, MJ

机构：

[1] McMaster Univ, Dept Chem, Hamilton, ON L8S 4M1, Canada

[2] Univ Coll Dublin, Dept Chem, Dublin 4, Ireland

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 05期

关键词：

D O I：

10.1021/ol049967o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：787 / 790

页数：4

共 27 条

[1] Sterically hindered organometallics:: multi-n-rotor (n=5, 6 and 7) molecular propellers and the search for correlated rotations [J].