Access

You are not currently logged in.

Access your personal account or get JSTOR access through your library or other institution:

login

Log in to your personal account or through your institution.

If You Use a Screen Reader

This content is available through Read Online (Free) program, which relies on page scans. Since scans are not currently available to screen readers, please contact JSTOR User Support for access. We'll provide a PDF copy for your screen reader.

Arylation of 2,2-Dimethyl-2H-1-Benzopyrans with Arylpalladium Complexes: A New Synthesis of the 4-Aryl-2,2-Dimethyl-2H-1-Benzopyran (Neoflavene) Ring System

D. V. Tyndall, J. P. Acton and M. J. Meegan
Proceedings of the Royal Irish Academy. Section B: Biological, Geological, and Chemical Science
Vol. 89B (1989), pp. 241-250
Published by: Royal Irish Academy
Stable URL: http://www.jstor.org/stable/20494510
Page Count: 10
  • Read Online (Free)
  • Download ($10.00)
  • Subscribe ($19.50)
  • Cite this Item
Since scans are not currently available to screen readers, please contact JSTOR User Support for access. We'll provide a PDF copy for your screen reader.
Arylation of 2,2-Dimethyl-2H-1-Benzopyrans with Arylpalladium Complexes: A New Synthesis of the 4-Aryl-2,2-Dimethyl-2H-1-Benzopyran (Neoflavene) Ring System
Preview not available

Abstract

The arylation of 2,2-dimethyl-2H-1-benzopyran with 2-chloromercuriophenols in the presence of lithium chloropalladite affords 4-aryl-2,2-dimethyl-2H-1-benzopyrans. To confirm the position of arylation in this reaction an unambiguous synthesis of a 2,2-dimethyl-3-phenyl-2H-1-benzopyran and a 2,2-dimethyl-4-phenyl-2H-1-benzopyran was carried out. 3-Aryl-2H-1-benzopyran-2-ones were treated with methylmagnesium iodide to give the 3-aryl-2,2-dimethyl-2H-1-benzopyran products, while 6,7-dimethoxy-4-phenyl-2H-1-benzopyran-2-one was reacted with methylmagnesium iodide to afford the 6,7-dimethoxy-2,2-dimethyl-4-phenyl-2H-1-benzopyran. Comparison of the ¹H and ¹³C n.m.r data of these products with those obtained from the Heck arylation reaction confirmed that arylation of 2,2-dimethyl-2H-1-benzopyran had occurred at C-4 This reaction offers a new synthetic route to the neoflavene ring system.

Page Thumbnails

  • Thumbnail: Page 
[241]
    [241]
  • Thumbnail: Page 
242
    242
  • Thumbnail: Page 
243
    243
  • Thumbnail: Page 
244
    244
  • Thumbnail: Page 
245
    245
  • Thumbnail: Page 
246
    246
  • Thumbnail: Page 
247
    247
  • Thumbnail: Page 
248
    248
  • Thumbnail: Page 
249
    249
  • Thumbnail: Page 
250
    250