Journal of the Chemical Society. Perkin transactions I p. 2287 - 2289 (1981)
Update date:2022-08-29
Topics:
Spangler, Charles W.
Kjell, Douglas P.
Wellander, Lori L.
Kinsella, Mary A.
Methyltriphenoxyphosphonium iodide (MTPI) is an effective dehydration and dehydrohalogenation reagent under mild conditions when 1,3-dimethylimidazolidin-2-one is used as an aprotic solvent in place of the more normally used hexamethylphosphoric triamide (HMPT).Since previosly suggested mechanisms had proposed alcohol-HMPT interaction as an important mechanistic step, this result coupled with comparative product geometric isomer distributions and the conjugated: non-conjugated triene product ratios leads to the conclusion that MTPI-alcohol interaction with displacement of phenoxide is the primary step in the reaction.In dimethyl sulphoxide (DMSO) alcohol dehydratation is hindered by DMSO-MTPI interaction yielding dimethyl sulphide.
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