References

Our Paper

Cha, J. Y.; Yeoman, J. T. S.; Reisman, S. E. J. Am. Chem. Soc. 2011, 133, 14964-14967.

Similar Reaction to Ours

Mereyala, H. B.; Goud, P. M.; Gadikota, R. R.; Reddy, K. R. J. of Carbohydrate Chem., 2000, 19, 1211-1222.

The authors of this article discuss how by using triphenylphosphine, imidazole, and iodine, OH groups can either be transformed into epoxides and alkenes.

Imidazole is a molecule that is slightly basic, triphenylphosphine can easily be oxidized, and iodine is a nucleophile. In all of these reactions we think that the imidazole deprotonates one of the oxygens which then gains a negative charge. For step A the triphenylphosphine bonds with the negatively charged oxygen then the carbon bonds to the other oxygen to avoid being a cation and the oxygen has a positive charge. The H is grabbed by another imidazole, and product II is complete. In step B, the mechanism is similar expect that another oxygen is lost and a double bond forms between the carbons.

Articles Citing this Paper

Kunig, J.; L�nnecke, P.; Hey-Hawkins, E. Carbohydrate Research, 2011, 9, 1154-1160.

The above article was cited because Kunig et all are working on monosaccharides and forming different derivatives to study different substituted glycosidic precursors.

Jereb, M.; Vra�ic, D.; Zupan, M. Tetrahedron, 2011, 7, 1355-1387.

The above article was cited by Jereb et all because this article mentions the different uses of iodine and how it has become more popular of a molecule since researches have found many uses for it chemically, and it is a “green” alternative to many other catalysts.

Banda, G,; Chakravarthy, I. E.; Tetrahedron: Asymmetry, 2006, 11, 1684-1687.

This article mentions how to turn bisacetonide mannofuranolactone into different lactones in which they use the mechanism mentioned in our main article.

Retreat!