Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5283064 | Tetrahedron Letters | 2006 | 4 Pages |
Abstract
The nucleophilic aromatic substitution of 1,5-difluoro-2,4-dinitrobenzene with 2-propylresorcinol in Et3N/CH3CN produces a mixture of syn and anti conformers of the cyclic tetramer and the cyclic hexamer with a kinetically controlled product distribution. Moreover, the reaction in DMF was catalyzed by CsF to also produce a mixture of these cyclic oligomers. In this case, however, the C-O bond is cleaved by the fluoride ion and the cyclization reaction is reversible; therefore, in the presence of excess CsF, the thermodynamically favored product (syn-isomer of cyclic tetramer) is obtained as the major product. The structures of the two conformational isomers of cyclic tetramers were determined by X-ray crystallography.
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Authors
Hisatoshi Konishi, Kazunari Tanaka, Yuki Teshima, Takayuki Mita, Osamu Morikawa, Kazuhiro Kobayashi,