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A reviewer has pointed out that while the mechanism shown in Scheme 2 is not unreasonable, there is no real evidence for the proposed electrophilic addition of 2 to alkenes. An alternative possibility could involve an initial dehydration of 1 with acid to produce a reactive benzylic cation that would then undergo stepwise addition of styrene to eventually give 6. We found, however, that the N-methyl analogue of 1 did not undergo the substitution reaction with styrene and this observation provides good support for the requirement of a 2H-indol-2-one intermediate (i.e. 2).
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A reviewer has pointed out that while the mechanism shown in Scheme 2 is not unreasonable, there is no real evidence for the proposed electrophilic addition of 2 to alkenes. An alternative possibility could involve an initial dehydration of 1 with acid to produce a reactive benzylic cation that would then undergo stepwise addition of styrene to eventually give 6. We found, however, that the N-methyl analogue of 1 did not undergo the substitution reaction with styrene and this observation provides good support for the requirement of a 2H-indol-2-one intermediate (i.e. 2).
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84868263856
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Identical products were obtained in essentially the same yield by carrying out the intramolecular cyclization reaction with catalytic ptoluenesulfonic acid in toluene at 100 °C
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Identical products were obtained in essentially the same yield by carrying out the intramolecular cyclization reaction with catalytic ptoluenesulfonic acid in toluene at 100 °C
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