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. 2005 Jan 12;127(1):293-8.
doi: 10.1021/ja044814h.

Selective monoprotection of 1,n-terminal Diols in supercritical carbon dioxide: a striking example of solvent tunable desymmetrization

Peter Licence  1 , William K Gray, Maia Sokolova, Martyn Poliakoff
Affiliations

Selective monoprotection of 1,n-terminal Diols in supercritical carbon dioxide: a striking example of solvent tunable desymmetrization

Peter Licence et al. J Am Chem Soc. .

Abstract

The reaction between 1,n-terminal diols (n = 3 or 6) with simple alcohols (MeOH, EtOH, and n-PrOH) in supercritical CO(2) over an acid catalyst (Amberlyst 15) leads to two possible products, a mono- and a bis-ether. At 150 degrees C, the selectivity of the reaction with 1,6-hexanediol and MeOH can be switched from 1:20 in favor of the bis-ether at 50 bar to 9:1 in favor of the desymmetrized mono-ether at 200 bar. It is demonstrated that the switch in selectivity is associated with the phase state of the reaction mixture, with monophasic conditions favoring the mono-ether and biphasic conditions favoring the bis-ether. A rationalization of this effect is also presented.

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