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)vinyl halides.
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The reactions of 1-aryl-2,2-bis(<I>o</I>-methoxyphenyl)vinyl halides (<B>4</B>)–(<B>7</B>) in 80% aqueous ethanol (80% EtOH), acetic acid (AcOH), or 70% aqueous <I>N</I>,<I>N</I>-dimethylformamide gave benzofurans (<B>8</B>)–(<B>10</B>), respectively. The kinetic results <I>i.e.</I>, 1) first-order reaction rates, 2) large α-substituent effect (ρ=−4.12 against σ<SUP>+</SUP>), 3) large leaving group effect (<I>k</I><SUB>Bt</SUB>⁄<I>k</I><SUB>Cl</SUB>=85 in 80% EtOH and 28 in AcOH) and 4) the solvent effect (m=0.53), are consistent with the formation of the intermediate vinyl cations (<B>3</B>) which are captured exclusively by the β-<I>o</I>-methoxyl group. In the reaction of vinyl bromide (<B>7</B>), the formation of 7–9% of benzofuran (<B>11</B>) results from the β-<I>o</I>-methoxyphenyl migration in the vinyl cation (<B>17</B>) followed by cyclization. The exclusive intramolecular cyclization of the vinyl cations is discussed in terms of the proximity effect of the β-<I>o</I>-methoxyl group.
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