Iodination of methoxyacetone yields initially 1-iodo-3-methoxypropanone, which then rearranges to its 1,1-isomer; the latter product is favoured thermodynamically by a factor of 2.9 × 105 as a result of a stabilising interaction between geminal iodine and oxygen atoms.
R. A. M. O'Ferrall and B. A. Murray, J. Chem. Soc., Chem. Commun., 1988, 1098 DOI: 10.1039/C39880001098
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