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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 19, Number 10
BKCSDE 19(10)
October 20, 1998 

Anchimeric Assistance in the Rearrangement of Dichloro-3-methyl-1,4-oxathianes to 2-Chloromethyl Dihydro-1,4-oxathiins
Hoh-Gyu Hahn, Joong-Kwon Choi, Kee Dal Nam
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.
1109 - 1113
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