Posts Tagged ‘chemical knowledge’

Secrets of a university tutor. An exercise in mechanistic logic, prequel.

Saturday, October 27th, 2012

The reaction below plays a special role in my career. As a newly appointed researcher (way back now), I was asked to take tutorial groups for organic chemistry as part of my duties. I sat down to devise a suitable challenge for the group, and came upon the following reaction[1]. I wrote it down on page 2 of my tutorial book, which I still have. I continue to use this example in tutorials to this day, some 35 years later.

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References

  1. T.C. Clarke, and R.G. Bergman, "Olefinic cyclization at a vinyl cation center. Inversion preference for intramolecular nucleophilic substitution by a double bond", J. Am. Chem. Soc., vol. 94, pp. 3627-3629, 1972. http://dx.doi.org/10.1021/ja00765a062