Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Menschutkin Reaction in Liquid Sulfur Dioxide
Niichiro TokuraYasuhiko Kondo
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1963 Volume 36 Issue 2 Pages 200-204


1) The Menschutkin reaction (reaction of methyl, ethyl or isopropyl iodide with pyridine, dimethylaniline or dimethyl-o-toluidine) has been carried out in liquid sulfur dioxide. The reaction rate has been compared with those in other commonly used solvents.
2) The reaction rate in liquid sulfur dioxide is the slowest, whereas the previously performed reactions such as the Beckmann rearrangement and the cationic polymerization in this solvent were the fastest among the solvents ordinarily used.
3) The reason for such a discrepancy has been discussed. Importance of the Bare (or unsolvated) ion or species in an ionic reaction is presented.

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