title: Synthesis of isotopically labeled 1,3-dithiane.
abstract: The 1,3-dithiane is a protected formaldehyde anion equivalent that could serve as a useful labeled synthon. We report a facile synthesis of 1,3-[2-(13)C]- and 1,3-[2-(13)C, 2-(2)H2]dithiane in two steps from [(13)C]- or [(13) C, (2)H3 ]methyl phenyl sulfoxide. We have previously reported the high yield synthesis of [(13)C]methyl phenyl sulfide from [(13)C]MEOH and the oxidation of [(13)C]methyl phenyl sulfide to [(13)C]methyl phenyl sulfoxide. Here, we describe the facile exchange of deuterium from (2) H2 O into [(13)C]methyl phenyl sulfoxide to yield [(13)C, (2)H3]methyl phenyl sulfoxide. Thus, from [(13)C]MEOH and (2)H2O, all possible C2 stable isotopomers of 1,3-dithiane are available. Our synthetic route is also amenable to preparation of radiolabeled 1,3-dithianes.
authors.affiliation: Bioscience Division, Los Alamos National Laboratory, The National Stable Isotope Resource, MS E529, Los Alamos, NM, 87545, USA; Department of Chemistry, New Mexico Highlands University, Box 9000, Las Vegas, NM, 87701, USA.
authors.forename: Rodolfo A
authors.initials: RA
authors.lastname: Martinez
authors.forename: David R
authors.initials: DR
authors.lastname: Glass
authors.forename: Erick G
authors.initials: EG
authors.lastname: Ortiz
authors.forename: Marc A
authors.initials: MA
authors.lastname: Alvarez
authors.forename: Clifford J
authors.initials: CJ
authors.lastname: Unkefer
mesh_terms: D002247:Carbon Isotopes / Q000138:chemical synthesis* / Q000302:isolation & purification*; D007553:Isotope Labeling / Q000379:methods; D011807:Quinolizines / Q000138:chemical synthesis* / Q000302:isolation & purification*; D019275:Radiopharmaceuticals / Q000138:chemical synthesis / Q000302:isolation & purification; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000302:isolation & purification*
chemical_list: D002247:Carbon Isotopes; D011807:Quinolizines; D019275:Radiopharmaceuticals; D013457:Sulfur Compounds; C438055:dithiane
keywords: 13C-labeled synthons; stable isotope labeling