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Research - Dr. Justik’s Group. Synthesis and Structure of Hypervalent Iodine Compounds. Hypervalent Iodine Compounds. The concept “ hypervalent iodine ” refers to the unique bonding interaction in iodine(III) and (V) compounds:. Hypervalent Iodine Compounds.

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research dr justik s group

Research - Dr. Justik’s Group

Synthesis and Structure of Hypervalent Iodine Compounds

hypervalent iodine compounds
Hypervalent Iodine Compounds
  • The concept “hypervalent iodine” refers to the unique bonding interaction in iodine(III) and (V) compounds:
hypervalent iodine compounds1
Hypervalent Iodine Compounds
  • Hypervalent iodine oxidants were the original “green” reagents replacing many toxic metals (lead and thallium) in important synthetic transformations:
resaerch interests
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

slide5
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

synthesis with hypervalent iodine
Synthesis with Hypervalent Iodine

Improving “green” methods with HMBI - MWJ

synthesis with hypervalent iodine2
Synthesis with Hypervalent Iodine
  • Heterocyclic Synthesis
synthesis with hypervalent iodine3
Synthesis with Hypervalent Iodine
  • Heterocyclic Synthesis (Melanie Knowlton ’10, Rachael Carmichael ‘12)
synthesis with hypervalent iodine4
Synthesis with Hypervalent Iodine
  • Attempted Heterocyclic Synthesis – (Heather Sopher ‘09, Samantha Kristufek ’11?)
synthesis with hypervalent iodine5
Synthesis with Hypervalent Iodine
  • Attempted Heterocyclic Synthesis – (Heather Sopher ‘09, Samantha Kristufek ’11)
synthesis with hypervalent iodine6
Synthesis with Hypervalent Iodine
  • Heterocyclic Synthesis
synthesis with hypervalent iodine7
Synthesis with Hypervalent Iodine
  • Synthesis of a Novel Phenyliodonium Betaine - MWJ
synthesis with hypervalent iodine8
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

synthesis with hypervalent iodine9
Synthesis with Hypervalent Iodine
  • Other long-term targets of interest
structural studies
Structural Studies
  • Structural Confirmation of an alkenyliodonium salt with a pyridine N-oxide moiety
structural studies1
Structural Studies
  • Synthesis of a novel phenyliodinium betaine
structural studies2
Structural Studies
  • First example of a protonated iodosobenzene derivative
acknowledgements
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
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