Highly regioselective ring-opening of trisubstituted aziridines by sulfur-stabilised carbanions

Santiago Carballares, Donald Craig, Christopher J. T. Hyland, Pengfei Lu, Tanya Mathie, Andrew J. P. White
2009 Chemical Communications  
General experimental Melting points were determined using a Stuart Scientific SMP1 melting point apparatus and are uncorrected. Infrared spectra were recorded on a Mattson 5000 FTIR spectrometer and on a Perkin-Elmer Spectrum RX FT-IR System. Proton magnetic resonance ( 1 H NMR) and carbon magnetic resonance ( 13 C NMR) spectra were recorded in CDCl 3 unless otherwise stated on a Jeol GSX-270, a Bruker DRX-300, a Bruker AV-400 or a Bruker AV-500 spectrometer. Chemical shifts are in part per
more » ... are in part per million (ppm) and are referenced relative to the residual proton-containing solvent ( 1 H NMR: 7.26 ppm for CDCl 3 ; 13 C NMR: 77.0 ppm for CDCl 3 ). The following abbreviations are used to indicate the multiplicities: s, singlet, bs, broad signal; d, doublet; t, triplet; m multiplet. Mass spectra (CI) were recorded using Micromass AutoSpec-Q, Micromass Platform II or Micromass AutoSpec Premier instruments. Elemental analyses were performed at the microanalytical laboratory of the London Metropolitan University. Analytical thin layer chromatography (TLC) was performed on pre-coated aluminium-backed Merck Kiesegel 60 F 254 plates. Visualisation was effected with ultraviolet light, potassium permanganate or vanillin as appropriate. Flash chromatography was performed using BDH (40-63 μm) silica gel unless otherwise stated. DMSO and CH 2 Cl 2 were distilled under nitrogen from CaH 2 prior to use. All other solvents were reagent-grade. Petrol refers to the fraction with bp 760 40-60 °C. All liquid reagents except HCl and Me 2 S were distilled prior to use. KOAc was oven-dried at 120 °C for several days prior to use. All other reagents were purchased from Aldrich, Fluka, Acros, Alfa Aesar Lancaster and used as such unless otherwise stated. Microwave reactions were performed using a Biotage Initiator instrument. (E)-4-(4-Methoxyphenyl)but-2-en-1-ol 1
doi:10.1039/b815971h pmid:19137182 fatcat:pyiiw5i4n5cvzgxhx22p5e4tha