Tetrahedron

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

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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.

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