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- W1966103732 abstract "The influence of a β-methyl group on the reactivity of two stereoisomeric vinyl bromides has been studied. In 80% ethanol cis-(8) and trans-α-bromoanethole (9) undergo first order reactions leading to p-methoxypropiophenone (15), 1-ethoxy-1-(p-anisyl)-propene (16) and p-anisylpropyne (12). Solvolysis of the cis isomer 8 is accompanied by isomerization to the more stable trans isomer 9 which is approx. eight times less reactive than 8. Cis-trans isomerization is also observed in nitrobenzene at 150°. These results are in agreement with the unimolecular substitution-elimination (SN1−E1) mechanism which competes with cis-trans isomerization at the ion pair stage. The solvolysis rate of 9 is slightly lower and that of 8 somewhat higher than the rate of α-bromo-p-methoxystyrene (3c). In the absence of other effects a β-methyl group therefore slightly depresses the ionization rate, presumably by steric hindrance of solvation. These results confirm the negligible polar influence of a β-methyl substituent on the stability of vinyl cations." @default.
- W1966103732 created "2016-06-24" @default.
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- W1966103732 date "1971-12-10" @default.
- W1966103732 modified "2023-10-17" @default.
- W1966103732 title "Solvolysis and Isomerization ofcis- andtrans-1-Bromo-1-(p-anisyl)-propene (?-Bromoanethole) Mesomeric Vinyl Cations, Part V" @default.
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- W1966103732 doi "https://doi.org/10.1002/hlca.19710540816" @default.
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