Research - Dr. Justik’s Group

1. Research - Dr. Justik’s Group Synthesis and Structure of Hypervalent Iodine Compounds

2. Hypervalent Iodine Compounds • The concept “hypervalent iodine” refers to the unique bonding interaction in iodine(III) and (V) compounds:

3. Hypervalent Iodine Compounds • Hypervalent iodine oxidants were the original “green” reagents replacing many toxic metals (lead and thallium) in important synthetic transformations:

4. Resaerch Interests Synthesis and Reactivity • Improvement of “green” synthetic methodology using hypervalent iodine • Exploration of hetereocyclic syntheses • Preparation of novel iodinanes of interest from an intellectual curiosity or synthetic challenge aspect • In collaboration with Dr. John Protasiewicz at Case Western Reserve University explore new iodinanes using X-ray crystallography • Characterize novel iodinanes of interest from an intellectual curiosity or synthetic challenge aspect Structure

5. Synthesis with Hypervalent Iodine 1H-1-hydroxy-5-methyl-1,2,3-benziodoxathiole 3,3-Dioxide HMBI A compact heterocyclic equivalent of HTIB MW 314.10 g/mol Hydroxy(tosyloxy)iodobenzene “Koser’s Reagent” HTIB A mild and useful oxidant that mimics elemental bromine MW 392.22 g/mol

6. Synthesis with Hypervalent Iodine Improving “green” methods with HMBI - MWJ

7. Synthesis with Hypervalent Iodine

8. Synthesis with Hypervalent Iodine • Heterocyclic Synthesis

9. Synthesis with Hypervalent Iodine • Heterocyclic Synthesis (Melanie Knowlton ’10, Rachael Carmichael ‘12)

10. Synthesis with Hypervalent Iodine • Attempted Heterocyclic Synthesis – (Heather Sopher ‘09, Samantha Kristufek ’11?)

11. Synthesis with Hypervalent Iodine • Attempted Heterocyclic Synthesis – (Heather Sopher ‘09, Samantha Kristufek ’11)

12. Synthesis with Hypervalent Iodine • Heterocyclic Synthesis

13. Synthesis with Hypervalent Iodine • Synthesis of a Novel Phenyliodonium Betaine - MWJ

14. Synthesis with Hypervalent Iodine • Synthesis of a Novel Phenyliodonium Betaine - MWJ Brianne Sawders (‘12) is currently exploring the limits of the Suzuki reaction with this betaine

15. Synthesis with Hypervalent Iodine • Other long-term targets of interest

16. Structural Studies • Structural Confirmation of an alkenyliodonium salt with a pyridine N-oxide moiety

17. Structural Studies • Synthesis of a novel phenyliodinium betaine

18. Structural Studies • First example of a protonated iodosobenzene derivative

19. Acknowledgements Former & Current Students: • Michelle Borkovec ‘06 – M.A. Drexel – Schoolteacher • Alyssa Zimmerman ‘08 – Meadowbrook Milk, Erie, PA. • Heather Sopher ‘09 – UC Irvine – Atmospheric Chem. • Michael Hughes ‘09 – Compunetics, Inc. Monroeville, PA. • Amanda Dechant ‘09 – Whole Foods, Northeast, PA. • Alex Eckstrom (biology) ‘08 – D.D.S. Student – U. of Pitt. • Melanie Knowlton ‘09 – Lord Corporation, Erie, PA. • Rocky Viggiano ‘09 – Ph.D. Student – Case Western Res. Univ. • Samantha Kristufek ‘11 – Ph. D. Student, Texas A&M • Danielle Bittner ‘11 – Ph. D. Student, Penn State • Rachael Carmichael ‘12 – M.S. Student - UNV Reno • Brianne Sawders ‘12 – Contract Chemist – PPG Industries