Ok i was going to the library anyways and i picked up.
Toda, F. and Shigemasa, T. "Pinacol rearrangements in the solid state". J Chem Soc. Perkin Trans, 1, 1989, 209-211
Abstract
The rearrangement of PhCH(OH)C(OH)PhR1 (R1 = Ph, tolyl, anisyl, ClC6H4) to mixts. of PhCOCHPhR1 and R1CPh2CHO was catalyzed by HCl, p-toluenesulfonic acid, and CCl3CO2H. The HCl-catalyzed rearrangement of MeCH(OH)C(OH)MePh, in a complex with a 2,2'-biphenyldicarboxamide deriv. host compd., gave MeCOCHMePh.
They were looking at these substituted reactions in this article --> PhCH(OH)C(OH)PhR1 (R1 = Ph, tolyl, anisyl, ClC6H4). This paper is really short and doesn't really apply to pur case, except for a few short statements at the end which reference the following paper which might bee more interesting.
F. Toda, A. Kati, Y. Tagami, and T.C. Mak, Chem. Lett., 1987, 1393.
But this paper does have one very interesting thing. They say the (dilute H2SO4 33wt% i think, under reflux at 112C)-catalyzed rearrangement of MeCH(OH)C(OH)MePh, yeilds MeCOCHMePh 48%, (Me)2CHCOPh 29%, OCHC(Me)2Ph 5%. Then they say that the same selectivity was observed by treating the above with p-TsOH in the solid state.
I wonder if this same effect is occuring in the isosassy diol rearrangement to give an alpha-methylphenylacetaldehyde contaminant?
Oh yes, one other thing. They got good rearramngement yeilds using dry HCl gas on the solids mentioned in the abstract.
Foxy
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