The reaction of rhenium (VII) trioxo complexes containing the ligand sets scorpionate, [HB(pz)3]ReO3 (6), [Ph-B(pz)3]ReO3 (7), and [[HC(pz)3]ReO3][ReO4] (8) and pyridine/pyridine-type ligands [(4,7-diphenyl-1,10-phen)(Br)ReO3] (12), [(4,4'-di-tert-butyl-2,2'-dipyridyl)(Cl)ReO3] (13), and [(py)2Re(Cl)O3] (4), with diphenyl ketene, has led to the isolation of six novel [3 + 2] cycloaddition products. These air-stable solids 9-11 and 15-17 are the result of [3 + 2] addition of the O=Re=O motif across the ketene C=C double bond. Five of the six [3 + 2] cycloaddition products have been structurally characterized by single-crystal X-ray diffraction and in all cases by 13C NMR and IR spectroscopies.

Drug profiling, or the ability to link batches of illicit drugs to a common source or synthetic route, has long been a goal of law enforcement agencies. Research in the past decade has explored drug profiling with isotope ratio mass spectrometry (IRMS). This type of research can be limited by the use of substances seized by police, of which the provenance is unknown. Fortunately, however, some studies in recent years have been carried out on drugs synthesized in-house and therefore of known history. In this study, 18 MDMA samples were synthesized in-house from aliquots of the same precursor by three common reductive amination routes and analyzed for 13C, 15N, and 2H isotope abundance using IRMS. For these three preparative methods, results indicate that 2H isotope abundance data is necessary for discrimination by synthetic route. Furthermore, hierarchical cluster analysis using 2H data on its own or combined with 13C and/or 15N provides a statistical means for accurate discrimination by synthetic route.

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All reagents and solvents were obtained from commercial suppliers and were used without further purification unless otherwise stated. Purification was carried out according to standard laboratory methods. 1 Tetrahydrofuran and diethyl ether were dried by heating to reflux over sodium wire, using benzophenone ketyl as an indicator, then distilled under nitrogen. Diethyl ether (for purification purposes) and petroleum ether 30-40 °C were used as obtained from suppliers without further purification. Din -butylmagnesium, n-Bu 2 Mg, 2 obtained as a 1M solution in heptane, was standardised using salicaldehyde phenylhydrazone as indicator. 3 Parent amines were dried by heating to 100 °C under vacuum (0.1 mbar) using a Kugelrohr apparatus for 2 h, before being purged with and stored under N 2 over 4 Ǻ molecular sieves. 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone) (DMPU) was dried by heating to reflux over calcium hydride and distilling under vacuum before being purged with and stored under N 2 over 4 Å molecular sieves. Chlorotrimethylsilane was distilled under N 2 and stored over 4 Å molecular sieves. 4-t-Butylcyclohexanone 1a and 4-phenylcyclohexanone 1d were recrystallised twice from dry hexane at 4 °C, purged with, and stored under N 2. 4-i-Propylcyclohexanone 1b, 4-n-propylcyclohexanone 1c, and 4-(tertbutyldimethylsiloxy)cyclohexanone 1e were dried by heating to reflux over calcium chloride and distilled under vacuum before being purged with and stored under N 2 over 4 Å molecular sieves.