Eastwood reaction

The di-O-tosylates (prepared by action of tosyl chloride in pyridine) are reduced with zinc (Nal/Zn route e Tipson-Cohen reaction) [13]. Cyclic ortho-esters (prepared by reaction of the diol with ethyl orthoformate) are transformed into olefins by simple heating in the presence of acids (Eastwood reaction, route b) [14]. Cyclic thiocarbonates (obtained by reaction of a diol with thiophosgene or (V,(V -thiocarbonyl-di-imidazole) are reduced to olefin with trimethyl phosphite (Corey-Winter method, route c) [15]. Finally, reduction of vicinal di-xanthates with tri- -butyltin hydride according to the Barton procedure [16] affords olefins via a reductive elimination process route a). The Corey-Winter, Garegg, and Tipson-Cohen methods are most commonly applied for deoxygenation of sugar diols. 

Das, K. M., Eastwood, M. A., McManus, J. P., and Sircus, W. (1973) Adverse reactions during salicylazosidfapyridine therapy and the relation with drug metabolism and acetylator phenotype. New England Journal of Medicine. 289, 491 95. 

Eastwood SL, Burnet PW, Harrison PJ. 1997. GluR2 glutamate receptor subunit flip and flop isoforms are decreased in the hippocampal formation in schizophrenia A reverse transcriptase-polymerase chain reaction (RT-PCR) study. Brain Res Mol Brain Res 44 92-98. 

Dimethylamino-l,3-dioxolanes, prepared by the reaction of the diol with dimethylformamide di-methylacetal, react in situ with Mel to give quaternary ammonium salts, which typically fragment at lower temperature (110-130 C) to give the alkene, CO2 and MeaNHI. For acid sensitive compounds such as the unsaturated acetal (46 equation 9), these conditions are superior to the original Eastwood procedure. Fragmentation of the 2-dimethylamino-1,3-dioxolane can also be effected by Ac20 and in some cases this modification is preferred, since the weakly nucleophilic acetate by-product causes fewer serious side reactions than iodide. ... 

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