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One referee surmised that molecular chlorine might be the active species in our system and advised us to check this possibility by carrying out the reaction showed in Scheme 3 in the presence of 4 Å MS. Accordingly, 4′-methylacetophenone was treated with 1.1 equivalents of molecular chlorine in ethylene glycol in the presence of 4 Å MS at room temperature. After 20 hours, 48% of starting material was recovered and only 7% of the desired cyclic ketal of α-chloroketone was obtained, together with 2-methyl-2-p-tolyl-1,3-dioxolane, which formed as the major product (40, Apparently, this result is distinct from that observed with our PhICl2/ethylene glycol/4 Å MS system under which the same cyclic ketal of α-chloroketone was obtained in 95% yield within only 30 minutes Table 1, entry 5, Therefore, we believe that the mechanism shown in Scheme 1 is still preferable
-
2/ethylene glycol/4 Å MS system under which the same cyclic ketal of α-chloroketone was obtained in 95% yield within only 30 minutes (Table 1, entry 5). Therefore, we believe that the mechanism shown in Scheme 1 is still preferable.
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