Studies of carbenium ion on unsaturated carbon. II. Exclusive formation of benzofurans via vinyl cations in the solvolytic reactions of 1-aryl-2, 2-bis (o-methoxyphenyl) …

T Sonoda, S Kobayashi, H Taniguchi

Index: Sonoda,T. et al. Bulletin of the Chemical Society of Japan, 1976 , vol. 49, p. 2560 - 2566

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Citation Number: 21

Abstract

The reactions of 1-aryl-2, 2-bis (o-methoxyphenyl) vinyl halides (4)–(7) in 80% aqueous ethanol (80% EtOH), acetic acid (AcOH), or 70% aqueous N, N-dimethylformamide gave benzofurans (8)–(10), respectively. The kinetic results ie, 1) first-order reaction rates, 2) large α-substituent effect (ρ=− 4.12 against σ+), 3) large leaving group effect (k Bt⁄ k Cl= 85 in 80% EtOH and 28 in AcOH) and 4) the solvent effect (m= 0.53), are consistent with the ...