64 Oxidations and Chlorinations of Isotopically-Labeled Alkyl Phenyl Sulfides

Wednesday, November 4, 2009
Ballroom A+B (Camino Real Hotel)
Carlos Herrera , Department of Natural Sciences, New Mexico Highlands University, Las Vegas, NM
David R Glass , Department of Natural Sciences, New Mexico Highlands University, Las Vegas, NM
Merritt C. Helvenston , Department of Natural Sciences, New Mexico Highlands University, Las Vegas, NM
Rodolfo A Martinez , Department of Natural Sciences, New Mexico Highlands University, Las Vegas, NM

Oxidations and Chlorinations of Isotopically-Labeled Alkyl Phenyl Sulfides

We have used [13C]methyl phenyl sulfide to produce a number of new isotopically-labeled precursors. From this chemistry we have produced over 100 new isotopically-labeled materials that are useful for the production of compounds that have been used in the fields of NMR-based quantum computing, polymer sciences, forensics, metabolism, protein structure determinations and medical diagnostics. We have developed a large scale (moles) one-pot, high-yield process of converting [13C]methanol to [13C]methyl phenyl sulfide.

The advantage of using [13C]methyl phenyl sulfide for the delivery of a labeled carbon is that as detailed below it be can used as a nucelophilic carbon or an electrophilic carbon.  By adjusting the

oxidation state of the sulfur (sulfoxide and sulfone) the acidity of the methyl protons is increased and a variety of bases can be used to accommodate specific reaction conditions.  We have found a variety of conditions for the transformations illustrated above and these will be discussed in our presentation.

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