Synthesis and Properties of Fluoroazulenes. II. Electrophilic Fluorination of Azulenes with N-Fluoro Reagents.

T Ueno, H Toda, M Yasunami, M Yoshifuji

Index: Ueno, Tetsuya; Toda, Haruhiko; Yasunami, Masafumi; Yoshifuji, Masaaki Bulletin of the Chemical Society of Japan, 1996 , vol. 69, # 6 p. 1645 - 1656

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Citation Number: 28

Abstract

1-Fluoro-and 1, 3-difluoroazulenes were synthesized for the first time by the electrophilic fluorination of azulenes with N-fluoro reagents. Selective preparation of 1-fluoroazulenes were performed by the fluorination of methyl azulene-1-carboxylates, followed by demethoxycarbonylation in 100% H 3 PO 4. 2-Substituted azulenes were fluorinated in higher yields. In the 1 H NMR of 1-fluoroazulene, long-range J FH values were not ...