Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of High Refractive Spiroheterocyclic Derivatives Through Thioacetalization of Multi-Carbonyl Compounds

  • Ye, Ji-Myoung (Department of Advanced Materials for Information and Display, Pusan National University) ;
  • Maheswara, Muchchintala (Department of Advanced Materials for Information and Display, Pusan National University) ;
  • Do, Jung-Yun (Department of Advanced Materials for Information and Display, Pusan National University)
  • Received : 2012.03.13
  • Accepted : 2012.04.24
  • Published : 2012.08.20
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Abstract

Preparation of several new spirocyclic mercapto derivatives is described. Thiol protection on multi-carbonyl compounds allows of high sulfur content necessary to induce high refractive index. Condensation of 1,3-dimercapto-2-propanol and cyclohexanone followed by successive oxidation and thioacetalization affords a dispirocycle with four sulfurs. Selective S,S-protection of cyclohexane-1,4-dione is achieved with 1,3-dimercapto-2-propanol and 2,3-dimercapto-1-propanol to provide dispirocycles with four sulfurs. Olefine-oxidation of norbornene gives a useful dialdehyde intermediate which is transformed to 1,3-dithiolane for a linearly-bound-cyclic molecule. Refractive index of linearly-bound-cycles was below 1.60 and dispirocycles exhibited high refractive index of 1.57-1.69.

Keywords

References

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