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https://doi.org/10.1016/S0040-4039(02)02517-0
Title: | Formation of an aromatic indenide anion in a bridge-annelated [2.2]metacyclophanene: A novel and stereoselective nucleophilic addition to an acenaphthylene derivative | Authors: | Chen, P. Lai, Y.-H. |
Keywords: | Acenaphthyleno-metacyclophanene Aromatization Geometric strain Indenide anion Nucleophilic addition |
Issue Date: | 1-Jan-2003 | Citation: | Chen, P., Lai, Y.-H. (2003-01-01). Formation of an aromatic indenide anion in a bridge-annelated [2.2]metacyclophanene: A novel and stereoselective nucleophilic addition to an acenaphthylene derivative. Tetrahedron Letters 44 (1) : 23-26. ScholarBank@NUS Repository. https://doi.org/10.1016/S0040-4039(02)02517-0 | Abstract: | Treatment of the acenaphthyleno-annelated thiacyclophanene 4 with n-butyl lithium followed by quenching with methyl iodide unexpectedly afforded the ring-contracted adduct 6. A similar reaction between cyclophanene 2 and n-butyl lithium gave the adduct 14 indicating indirectly that in the former reaction the nucleophilic addition occurred after the Wittig-rearrangement of 4 to form the cyclophanene 13. The relief of geometric strain in the [2.2]metacyclophanene moiety induced by acenaphthyleno-annelation is believed to be the driving force for the nucleophilic attack. The sulfonium salt 7 prepared by methylation of compound 6 underwent a spontaneous Hofmann-elimination, in the absence of a base, to give the intermediate cyclophanediene 18 which valence isomerized to the near-planar dihydropyrene 9. © 2002 Elsevier Science Ltd. All rights reserved. | Source Title: | Tetrahedron Letters | URI: | http://scholarbank.nus.edu.sg/handle/10635/76205 | ISSN: | 00404039 | DOI: | 10.1016/S0040-4039(02)02517-0 |
Appears in Collections: | Staff Publications |
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