S RN 1C-arylation of potassium aryloxides by arylazo phenyl or tert-butyl sulfides in DMSO
G Petrillo, M Novi, CD Erba, C Tavani, G Berta
Index: Petrillo, Giovanni; Novi, Marino; Dell Erba, Carlo; Tavani, Cinzia; Berta, Giovanni Tetrahedron, 1990 , vol. 46, # 23 p. 7977 - 7990
Full Text: HTML
Citation Number: 31
Abstract
Aryloxide ions (Ar'O-) behave as C-nucleophiles towards diazosulfides (ArN= NSR; R= Ph, But) leading to unsymmetrical hydroxybiaryls (ArAr'OH) via CC coupling. The reaction is particularly suited for the synthesis of terms which contain electron-withdrawing groups on the Ar moiety. The SRN1 mechanism is proposed on the grounds of experimental evidences.
Related Articles:
[Edson, Joseph B.; Wang, Zhigang; Kramer, Edward J.; Coates, Geoffrey W. Journal of the American Chemical Society, 2008 , vol. 130, # 14 p. 4968 - 4977]
Acid-catalyzed solvolysis of N-sulfonyl-and N-acyl-O-arylhydroxylamines. Phenoxenium ions
[Endo, Yasuyuki; Shudo, Koichi; Okamoto, Toshihiko Journal of the American Chemical Society, 1982 , vol. 104, # 23 p. 6393 - 6397]
Metal-Free Ortho C–H Borylation of 2-Phenoxypyridines under Mild Conditions
[Niu, Liting; Yang, Haijun; Wang, Ruji; Fu, Hua Organic Letters, 2012 , vol. 14, # 10 p. 2618 - 2621]
[Kuznetsova; Postnova; Koshel'; Lebedeva; Yun'kova Russian Journal of Organic Chemistry, 2004 , vol. 40, # 9 p. 1288 - 1290]
The Cyclic Dehydration of Biphenyl Derivatives to Fluorenes
[Anchel; Blatt Journal of the American Chemical Society, 1941 , vol. 63, p. 1948,1952]