Abstract
1,4-Dichloro-1,4-diazoniabicyclo[2,2,2]octane bis-chloride has been used as effective reagent for the chlorination of 3-arylsydnones to their corresponding 4-chloro derivatives in DMF-H2O at room temperature. The 1,4-diazabicyclo [2,2,2]octane was regenerated, rechlorinated and reused several times.
Keywords
References
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