Current time in Korea 18:41 Sep 19 (Sat) Year 2020 KCS KCS Publications
KCS Publications
My Journal  Log In  Register
HOME > Search > Browsing(BKCS) > Archives

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 

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