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Selective Oxidation of 25,27-di-(3’-formylphenoxylethoxy)- p - tert -butylcalix[4]arene

Selective Oxidation of 25,27-di-(3’-formylphenoxylethoxy)- p - tert -butylcalix[4]arene. Selective Oxidation of 25,27-di-(3’-formylphenoxylethoxy)- p - tert -butylcalix[4]arene. Selective Oxidation of 25,27-di-(3’-formylphenoxylethoxy)- p - tert -butylcalix[4]arene.

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Selective Oxidation of 25,27-di-(3’-formylphenoxylethoxy)- p - tert -butylcalix[4]arene

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  1. Selective Oxidation of25,27-di-(3’-formylphenoxylethoxy)-p-tert-butylcalix[4]arene Selective Oxidation of25,27-di-(3’-formylphenoxylethoxy)-p-tert-butylcalix[4]arene Selective Oxidation of25,27-di-(3’-formylphenoxylethoxy)-p-tert-butylcalix[4]arene Selective Oxidation of25,27-di-(3’-formylphenoxylethoxy)-p-tert-butylcalix[4]arene Selective Oxidation of25,27-di-(3’-formylphenoxylethoxy)-p-tert-butylcalix[4]arene Selective Oxidation of25,27-di-(3’-formylphenoxylethoxy)-p-tert-butylcalix[4]arene Selective Oxidation of25,27-di-(3’-formylphenoxylethoxy)-p-tert-butylcalix[4]arene Selective Oxidation of25,27-di-(3’-formylphenoxylethoxy)-p-tert-butylcalix[4]arene Selective Oxidation of25,27-di-(3’-formylphenoxylethoxy)-p-tert-butylcalix[4]arene Selective Oxidation of25,27-di-(3’-formylphenoxylethoxy)-p-tert-butylcalix[4]arene • By Selective Oxidation of25,27-di-(3’-formylphenoxylethoxy)-p-tert-butylcalix[4]arene Mr. Rojrit Rojanathanes Assist.Prof.Dr. Tawatchai Tuntulani Dr. Mongkol Sukwattanasinitt* http://www.student.chula.ac.th/~b3819023

  2. Overview Introduction Experiment Discovery Application

  3. Introduction Dialdehyde Calix[4]arene, the key intermediate Calix[4]arene, the molecular platform Na+

  4. K2CO3, CH3CN, Bu4N+Br- Synthesis of (1) Compound (1) 60 %

  5. Ph3P=CH2 Grubb’s catalyst Aniline hn KCN Zn(Hg)/HCl Stilbene Formation

  6. KCN EtOH Aldehyde Coupling Compound (7) 42 %

  7. KCN EtOH KCN Coupling The Serendipity The Serendipity The Serendipity The Serendipity The Serendipity

  8. 1H-NMR 9.93 OR 9.96 1.40

  9. OEt 13C-NMR 192.1 192.1 14.2 53.2 166.4

  10. NOESY HMBC 2D-NMR

  11. KCN EtOH Surprise Oxidation Surprise Oxidation Surprise Oxidation Surprise Oxidation Surprise Oxidation Compound (2) 50 %

  12. KCN i-PrOH Synthesis of (3) Compound (3) 31 %

  13. KCN EtOH Aldehyde Coupling + Compound (9) 20 % Compound (8) 42 %

  14. KOH EtOH Cannizzaro Reaction Compound (4) 4 % Compound (5) 16 % Compound (6) < 16 % >

  15. KCN EtOH Selective Oxidation Compound (2) 50 %

  16. - - + - - - - - - Related Oxidation +

  17. - - H+ -H+ -CN - Baeyer - Villiger Mechanism Possible Mechanism

  18. + + + + EtOH - - - - Esterification

  19. Discovery Selective oxidation of dialdehyde calix[4] arene via KCN catalyst in the presence of O2 The in situ esterification of acid calix[4] arene via phenolic protons on the lower rim

  20. Potential Application Synthesis new calix[4]arene derivatives De-symmetrized calix[4]arene Synthesis new selective ionophore

  21. Acknowledgement National Science and Technology Development Agency The Thailand Research Fund Scientific and Technological Research Equipment Centre Dr.Pornthep Sompornpisut Assist.Prof.Dr.Theerayut Wilaiwan

  22. Thank you for your attention Available on the web www.student.chula.ac.th/~b3819023

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