Unexpected formation of 2,2‐dichloro‐N‐(chloromethyl)acetamides during attempted Staudinger 2,2‐dichloro‐β‐lactam synthesis

In the quest for 3,3‐dichloro‐β‐lactam building blocks, the serendipitous formation of 2,2‐dichloro‐ N ‐(chloromethyl)acetamides was observed. This peculiar reactivity was investigated in detail, both experimentally and computationally by means of Density Functional Theory (DFT) calculations. 2,2‐Dichloro‐ N ‐(chloromethyl)acetamides were thus shown to be formed experimentally through reaction of 2,2‐dichloroacetyl chloride with...