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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

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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


Research dr justik s group

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 iodine1

Synthesis with Hypervalent Iodine


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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