Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Anchimeric Assistance in the Rearrangement of Dichloro-3-methyl-1,4-oxathianes to 2-Chloromethy1 Dihydro-1,4-oxathiins

  • Published : 1998.10.20
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Abstract

An anchimeric assistance of anilide in the rearrangement of dichloro-1,4-oxathaines 1 to 2-chloromethyl dihydro-1,4-oxathiins 2 is described. The inductive effect of the carbonyl group of anilide was negligible in the rearrangement. A rate of the rearrangement depended on the basicity of anilide nitrogen. A hydrogen bonding between the anilide hydrogen and an oxygen atom of those substituents make the nitrogen less basic, resulting in the slower rearrangement.

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References

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