Posts Tagged ‘photochemical’

So near and yet so far. The story of the electrocyclic ring opening of a cyclohexadiene.

Tuesday, December 6th, 2011

My previous three posts set out my take on three principle categories of pericyclic reaction. Here I tell a prequel to the understanding of these reactions. In 1965, Woodward and Hoffmann[1] in their theoretical analysis (submitted Nov 30, 1964) for which the Nobel prize (to Hoffmann only of the pair, Woodward having died) was later awarded. But in the same year, Elias Corey[2] reported the conclusion of a project started several years earlier (first reported (DOI: 10.1021/ja00907a030, Nov 1, 1963) to synthesize the sesquiterpene dihydrocostunolide.

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References

  1. R.B. Woodward, and R. Hoffmann, "Stereochemistry of Electrocyclic Reactions", Journal of the American Chemical Society, vol. 87, pp. 395-397, 1965. http://dx.doi.org/10.1021/ja01080a054
  2. E.J. Corey, and A.G. Hortmann, "The Total Synthesis of Dihydrocostunolide", Journal of the American Chemical Society, vol. 87, pp. 5736-5742, 1965. http://dx.doi.org/10.1021/ja00952a037