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http://dx.doi.org/10.5012/bkcs.2012.33.8.2494

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)
Publication Information
Bulletin of the Korean Chemical Society / v.33, no.8, 2012 , pp. 2494-2498 More about this Journal
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
Spiro heterocycle; High refractive index; 1,3-Dithiolane; Polyacrylate film; Dispirocycle;
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