Bulletin of the Korean Chemical Society

  • 제19권10호
  • /
  • Pages.1109-1112
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  • 1998
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Anchimeric Assistance in the Rearrangement of Dichloro-3-methyl-1,4-oxathianes to 2-Chloromethy1 Dihydro-1,4-oxathiins

  • 발행 : 1998.10.20
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초록

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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참고문헌

  1. J. Am. Chem. Soc. v.118 Fife, T. H.;Bembi, R.;Natarajan, R.
  2. J. Am. Chem. Soc. v.72 Winstein, S.;Goodman, L.;Boschan, R.
  3. J. Org. Chem. v.52 Lee, W. S.;Park. O. S.;Choi, J. K.;Nam, K. D.
  4. U.S. Patent 3 393 202 Kulka, M.;Thiara, D. S.;Harrison, W. A.
  5. U.S. Patent 3 728 357 Knight, B. I.;Curcumelli-Rodostamo, M.;Kulka, M.;Schmeling, B. V.
  6. Tetrahedron v.52 Easton, C. J.;Hutton, C. A.;Merrett, M. C.;Tiekink, E. R. T.