Computational studies of the tropone natural products, thiotropocin, tropodithietic acid, and troposulfenin. Significance of thiocarbonyl-enol tautomerism.

@article{Greer2008ComputationalSO,
  title={Computational studies of the tropone natural products, thiotropocin, tropodithietic acid, and troposulfenin. Significance of thiocarbonyl-enol tautomerism.},
  author={Edyta M Greer and David Aebisher and Alexander D Greer and Ronald Bentley},
  journal={The Journal of organic chemistry},
  year={2008},
  volume={73 1},
  pages={280-3}
}
Computations provide insight to the stability and isomeric possibilities of thiotropocin, tropodithietic acid, and troposulfenin. Thiotropocin and tropodithietic acid contain a flat 7-membered ring and delocalized pi-bonds similar to those of tropylium ion (C(7)H(7)(+)). Troposulfenin is far less stable; it contains a puckered tropone ring and localized bonds similar to 1,3,5-cycloheptatriene. A facile 1,5-hydrogen shift suggests that thiotropocin and tropodithietic acid exist as a pair of… CONTINUE READING