The Synthesis of Four Isomeric Diiodo-m-xylenes. Their Isomerization in Sulfuric and Polyphosphoric Acids
- 1 October 1965
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 38 (10) , 1590-1595
- https://doi.org/10.1246/bcsj.38.1590
Abstract
Four isomeric diiodo-m-xylenes have been synthesized and their isomerization in concentrated acids investigated in order to elucidate the mechanism of the new rearrangement observed in the Jacobsen reaction of 2-iodo-m-xylene. 2,4- and 4,5-Diiodo-m-xylene, in the presence of cold sulfuric or hot polyphosphoric acid, isomerize to 4,6- and 2,5-diiodo-m-xylene respectively. All four isomers readily undergo disproportionation with hot sulfuric acid to give mixtures of tri- and tetraiodo-m-xylenes. No disproportionation has been observed in the reaction with polyphosphoric acid. The important role played by a sulfo group in this reaction has been discussed.Keywords
This publication has 5 references indexed in Scilit:
- On the Jacobsen Reaction. IV. Character and Reaction MechanismBulletin of the Chemical Society of Japan, 1963
- STEREOCHEMISTRY OF DIPHENYL COMPOUNDS. THE PREPARATION AND RESOLUTION OF 3,5,3′,5′-TETRA-METHYL-2,2′-DIFLUORO-6,6′-DIAMINODIPHENYL. XIVJournal of the American Chemical Society, 1931
- Ueber Nitro‐ und Brom‐Derivate der XylidineEuropean Journal of Inorganic Chemistry, 1901
- Ueber Synthesen mittels ChlorjodEuropean Journal of Inorganic Chemistry, 1895
- Bericht über PatenteEuropean Journal of Inorganic Chemistry, 1884