Elsevier, Tetrahedron Letters, 15(51), p. 2029-2031
DOI: 10.1016/j.tetlet.2010.02.048
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Carbocylic 1,3-dioximes react with acyl chlorides giving systems that may, upon heating, suffer [3,3]-sigmatropic rearrangements in high yields in only one of the oximes esters, yielding 1,3-dinitrogen-2-oxygen trisubstituted carbocycles. Use of more reactive electrophiles, such as p-toluenesulfonyl chloride and diethyl chlorophosphate, introduces the halogen at position 2, while cleaving the N–O bond of just one of the oxime functions.