V. K. Aggarwal et al. / Tetrahedron Letters 42 (2001) 1587–1589
1589
2. General procedure
Soc., Perkin Trans. 1 1998, 3399–3403; (c) Ha, H.-J.;
Kang, K.-H.; Suh, J.-M.; Ahn, Y.-G. Tetrahedron Lett.
1996, 37, 7069–7070.
N-(p-Tolylsulphonyl)-2-(p-chlorophenyl)aziridine (Table
1, entry 4): Diethyl zinc (1.1 M in toluene, 1.0 mL) was
added to a stirred solution of N-(p-chlorobenzyli-
dene)toluene-p-sulphonamide (0.29 g, 1.0 mmol),
chloroiodomethane (0.15 mL, 2.0 mmol) and tetra-
hydrothiophene (0.18 mL, 2.0 mmol) in CH2Cl2 (5 mL)
at room temperature under a positive pressure of
argon. After 16 h, the reaction mixture was quenched
with saturated aqueous NH4Cl (5 mL) and the reaction
products extracted into CH2Cl2 (3×10 mL). The com-
bined organic extracts were washed with tri-
ethanolamine (2N, 2×10 mL) and brine (10 mL), dried
(Na2SO4) and concentrated under reduced pressure.
Purification by flash chromatography (CH2Cl2) gave
N-(p-tolylsulphonyl)-2-(p-chlorophenyl)aziridine as a
white crystalline solid (0.22 g, 71%), mp 117–118°C
(hexane/EtOAc) [lit.17 115–116°C]; lH (250 MHz,
CDCl3) 2.33 (1H, d, J 4.6 Hz, CHH%N), 2.43 (3H, s,
PhCH3), 2.97 (1H, d, J 7.0 Hz, CHH%N), 3.72 (1H, dd,
J 7.0 and 4.6 Hz, ArCH), 7.14 (2H, br d, J 8.5 Hz,
ArH), 7.25 (2H, br d, J 8.5 Hz, ArH), 7.33 (2H, br d,
J 8.2 Hz, ArH), 7.85 (2H, d, J 8.2 Hz, ArH).
7. Aggarwal, V. K.; Ali, A.; Coogan, M. P. J. Org. Chem.
1997, 62, 8628–8629.
8. Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1959,
81, 4256.
9. (a) Aromatic N-Ts and N-SES imines were prepared as
described: McKay, W. R.; Proctor, G. R. J. Chem. Soc.,
Perkin Trans. 1 1981, 2435–2442; (b) Aliphatic N-Ts
imines were prepared as described: Chemla, F.; Hebbe,
V.; Normant, J.-F. Synthesis 2000, 75–77; (c) Anisidine-
derived imines were prepared as described: Diehl, H.;
Hach, C. C. Inorg. Synth. 1950, 3, 196–201.
10. 1-[2-(Methyloxy)phenyl]-2-phenylaziridine: Chloroiodo-
methane (0.15 mL, 2.0 mmol) was added to a solution of
diethyl zinc (1.1 M in toluene, 2.0 mL) in CH2Cl2 (9 mL)
at 0°C under argon. The solution was stirred for 10 min
before adding tetrahydrothiophene (0.27 mL, 3.0 mmol),
followed by a solution of N-benzylidine-o-anisidine (0.21
g, 1.0 mmol) in CH2Cl2 (1 mL). The mixture was then
allowed to warm to ambient temperature. After 16 h the
reaction was quenched with saturated aqueous NH4Cl
(10 mL) and the products were extracted into CH2Cl2
(3×15 mL), dried (Na2SO4) and concentrated under
reduced pressure. Purification by Kugelrohr distillation
(150°C/0.02 mmHg) gave title compound as a yellow oil
(0.23 g, 100%, 94% pure; inseparable from recovered
imine), wmax (NaCl disc, liquid film)/cm−1 2834
(CꢁOCH3), 1269 (CꢁO), 1028 (CꢁO); lH (250 MHz,
CDCl3) 2.42 (1H, dd, J 6.4 and 0.9 Hz, CHH%N), 2.50
(1H, dd, J 3.7 and 0.9 Hz, CHH%N), 3.07 (1H, dd, J 6.4
and 3.7 Hz, PhCH), 3.81 (3H, s, OCH3), 6.83–7.02 (4H,
m, ArH), 7.25–7.45 (5H, m, ArH); lC (63 MHz, CDCl3)
37.9, 42.0, 55.5, 111.2, 120.5, 120.7, 123.0, 126.4, 127.1,
128.3, 139.6, 143.1, 152.4; m/z (CI) 226 (MH+, 78%), 225
(85), 224 (100), 211 (13), 134 (88) (found: MH+, 226.1233.
C15H16NO requires MH+, 226.1232).
Acknowledgements
We thank Marco Ferrara, Emma Alonso and Chris
O’Brien for providing samples of imines, the EPSRC,
Zeneca Agrochemicals P.T.D. and Avecia for their
support.
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