biostudies-literatureWeatherford-Pratt JTDivision of ChemistryNational Institute of General Medical SciencesNIGMS NIH HHS35055-35068https://www.ebi.ac.uk/biostudies/studies/S-EPMC12464997biostudies-literatureUnknown147(38)Despite advances in reactions such as hydrogen isotope exchange (HIE) and reductive deuteration, achieving controlled and selective deuteration remains challenging. Moreover, the difficulty of developing successful deuteration platforms is compounded by a lack of means to assess the stereoisotopic purity of deuterated products. We previously reported a highly regio- and stereoselective approach for generating semideuterated cyclohexenes via tandem protonation (H⁺/D⁺) and reduction (H^-/D^-) sequences of a dihapto-coordinate tungsten-benzene complex. While NMR and HRMS analyses suggested successful deuterium incorporation, molecular rotational resonance (MRR) spectroscopy identified numerous over-, under-, and mis-deuteration impurities. At the timeJournal of the American Chemical SocietyOptimizing the Synthesis of Deuterated Isotopomers and Isotopologues of Cyclohexene using Molecular Rotational Resonance Spectroscopy.PMC12464997CHE-2100345R01 GM1322051R01GM132205Sonstrom REWeatherford-Pratt JTEricson MNHoldren MSMeng AQBrewster SEDickie DASmith JAPate BHHarman WDScolati HNfalseOptimizing the Synthesis of Deuterated Isotopomers and Isotopologues of Cyclohexene using Molecular Rotational Resonance Spectroscopy.Despite advances in reactions such as hydrogen isotope exchange (HIE) and reductive deuteration, achieving controlled and selective deuteration remains challenging. Moreover, the difficulty of developing successful deuteration platforms is compounded by a lack of means to assess the stereoisotopic purity of deuterated products. We previously reported a highly regio- and stereoselective approach for generating semideuterated cyclohexenes via tandem protonation (H⁺/D⁺) and reduction (H^-/D^-) sequences of a dihapto-coordinate tungsten-benzene complex. While NMR and HRMS analyses suggested successful deuterium incorporation, molecular rotational resonance (MRR) spectroscopy identified numerous over-, under-, and mis-deuteration impurities. At the time2025-01-01T00:00:00Z2025 Sep2026-06-03T21:21:22.909Z2026-05-01T03:10:50.117ZS-EPMC124649974093772310.1021/jacs.5c12001