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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 33, Number 8
BKCSDE 33(8)
August 20, 2012 

 
Title
Synthesis of High Refractive Spiroheterocyclic Derivatives Through Thioacetalization of Multi-Carbonyl Compounds
Author
Ji-myoung Ye, Muchchintala Maheswara, Jung Yun Do*
Keywords
Spiro heterocycle, High refractive index, 1,3-Dithiolane, Polyacrylate film, Dispirocycle
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. Olefineoxidation 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.
Page
2494 - 2498
Full Text
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