63 New Synthesis of Isotopically-Labeled Vinyl Systems

Wednesday, November 4, 2009
Ballroom A+B (Camino Real Hotel)
Erick Ortiz , 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

New Synthesis of Isotopically-Labeled Vinyl Systems

We have developed a new labeled reagent which makes the production of vinyl sulfide, sulfoxide, and sulfone a quick and easy process.  Scheme 1 below illustrates this new reagent.

Scheme 1

Deuterium can be introduced by a simple exchange reaction in deuterium oxide and potassium carbonate. By this process diethyl (phenylthio[13C]methyl) phosphonate, diethyl (phenylsufinyl [13C]methyl) phosphonate and diethyl (phenylsulfonyl[13C]methyl) phosphonate and the deuterated versions are easily produced.

The reagent can be used in an aqueous/dimethylsulfoxide mixture to produce isotopically labeled vinyl systems in one step in less than 20 minutes.  Scheme 2 illustrates this transformation.  The use of aqueous formaldehyde gives the vinyl systems used for our research that we describe below.

Scheme 2

The synthesis of a variety of labeled compounds from these vinyl systems will be discussed.

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