62 Synthesis of Isotopically-Labeled 1,3-Dithiane

Wednesday, November 4, 2009
Ballroom A+B (Camino Real Hotel)
Crystal Rae Ulibarri , 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
Erick Ortiz , Department of Natural Sciences, New Mexico Highlands University, Las Vegas, NM
Merritt 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

Synthesis of Isotopically-Labeled 1,3-Dithiane

The reagent 1,3-dithiane has been a very useful synthon for the production of aldehydes and ketones.  It is normally produced by the reaction of formaldehyde or its diethyl acetal with 1,3-propanedithiol.  The reported yields for these reactions are about 85%. 

We wanted to produce isotopically-labeled dithiane from a single source.  We have used [13C]methyl phenyl sulfoxide to accomplish our goal. The [13C]methyl phenyl sulfoxide can be treated with trifluoroacetic anhydride to give the Pummerer product which is then treated with 1,3-propanedithiol to give isotopically-labeled 1,3-dithiane.  This represents the first synthesis of isotopically-labeled 1,3-dithiane.  An additional advantage to the use of [13C]methyl phenyl sulfoxide for the production of 1,3-dithiane is that the deuterated isotopomer can also easily be produced as is shown below. 

The details of this work will be presented.

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