Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Rearrangement and trans-Elimination contrary to the Chugaev Reaction Rule. VIII. Thermal Rearrangement of 2-Alkenyl S-Alkyl Xanthate
KAZUNOBU HARANOTANEZO TAGUCHI
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1972 Volume 20 Issue 11 Pages 2348-2356

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Abstract
In general, S-alkyl xanthates of 2-alkenol thermally rearranged to the dithiolcarbonates accompanying allylic shift. When a mixture of two xanthates having different S-alkyl and O-alkenyl groups is allowed to rearrange thermally, no crossover products are obtained. A pair of position isomers did not transform to a same product, but to isomeric products with allylic shift respectively. 3-Aryl-substituted allylic xanthates, on the other hand, rearrange to the corresponding dithiolcarbonates without allylic shift. On the basis of these findings, mechanisms of the transformations are discussed.
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© The Pharmaceutical Society of Japan
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