In 2020 EUR J ORG CHEM published article about C BOND-CLEAVAGE; ELECTRON-RICH ARENES; AROMATIC HYDROGEN-EXCHANGE; LEAVING GROUP; H ALLYLATION; ACTIVATION; EFFICIENT; CATALYST; SUBSTITUTION; PROTONATION in [Paul, Dipankar; Chatterjee, Paresh Nath] Natl Inst Technol Meghalaya, Dept Chem, Bijni Complex, Shillong 793003, Meghalaya, India in 2020, Cited 50. The Name is 1,3-Dimethoxybenzene. Through research, I have a further understanding and discovery of 151-10-0. Recommanded Product: 151-10-0
An investigation of the unexpected lability of the Csp(3)-Csp(2)bond connecting 2,4,6-trimethoxyphenyl group and an allylic moiety is carried out. We observed that the catalytic presence of either Lewis or Bronsted acid can render such 2,4,6-trimethoxyphenyl group labile. Several nucleophiles were found to substitute the labile C-C bond in mild reaction conditions resulting in very good yields of the allylated products. Even in the absence of a nucleophile, intramolecular cyclization of the parent substrate under acidic activation caused the labile C-C bond to cleave. A major motivation of this study is to understand the lability of electron-rich aryl group in acidic medium, employing 2,4,6-trimethoxyphenyl moiety as a case study. A plausible mechanism is proposed after carrying out several control reactions as well as UV/Vis and(1)H NMR spectroscopic studies. This work provides an insight into the activation of electron-rich arenes as a labile entity in acidic medium while also adding a conceptually novel C-C bond breaking approach to the vast literature of allylation of arenes.
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Reference:
Isothiazole – Wikipedia,
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