@article{
author = "Vitnik, Vesna and Vitnik, Željko and Juranić, Ivan",
year = "2012",
abstract = "The extensive computation study was done to elucidate the mechanism of formation dibromoepoxide from cyclohexanone and bromoform. In this reaction, the formation of dihaloepoxide 2 is postulated as a key step that determines the distribution and stereochemistry of products. Two mechanistic paths of reaction were investigated: the addition of dibromocarbene to carbonyl group of ketone, and the addition of tribromomethyl carbanion to the same (C=O) group. The mechanisms for the addition reactions of dibromocarbenes and tribromomethyl carbanions with cyclohexanone have been investigated using ab initio HF/6-311++G** and MP2/6-311+G* level of theory. Solvent effects on these reactions have been explored by calculations which included a continuum polarizable conductor model (CPCM) for the solvent (H2O). The calculations showed that both mechanisms are possible and are exothermic, but have markedly different activation energies.",
publisher = "Springer, New York",
journal = "Journal of Molecular Modeling",
title = "Carbenic vs. ionic mechanistic pathway in reaction of cyclohexanone with bromoform",
volume = "18",
number = "10",
pages = "4721-4728",
doi = "10.1007/s00894-012-1468-2"
}