Chlorination Ritter reaction

The I2 addition to 3 in chlorinated solvents yields a mixture of isomeric 2,6-diiodobicy-clo[3.3.0]octanes (endo.exo-69 and endo,endo-7tt) (equation 71)22. When the reaction was carried out in aqueous acetonitrile under similar conditions, the formation of a mixture of acetamido derivatives 71 and 72, arising from iodocyclization followed by the capture of the iodonium ion by the solvent to give a Ritter reaction intermediate, accompanied the formation of products 69 and 70 (equation 72)22. 

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