Author:
Kim Kil‐Joong,Lee Hyi‐Seung,Kim Kyongtae
Abstract
AbstractThe reactions of 1‐aryl‐2,2,2‐trifluoroethanone oximes with tetrasulfur tetranitride (S4N4) in toluene at reflux gave 5‐aryl‐5‐trifluoromethyl‐4H‐1,3,2,4,6‐dithiatriazines 2, 1‐aryl‐2,2,2‐trifluoroethanonyliden‐aminosulfenamides 3 and sulfur in 0–37%, 7–53%, and 2–41% yields, respectively. Treatment of 2 with tributyltin hydride in the presence of azobisisobutyronitrile in benzene at 80° afforded 3 in excellent yields.
Reference18 articles.
1. Reactions of tetrasulfur tetranitride with bromomethyl ketones. One pot synthesis of 3,5‐diaroyl‐ and 3,5‐diacyl‐1,2,4‐thiadiazoles
2. J.ChoandK.Kim J. Chem. Soc. Perkin Trans. 1 2345(1993).
3. Reactions of Monohalomethyl Aryl Ketoximes with Tetrasulfur Tetranitride: Much Improved Synthesis of 3-Aryl-1,2,5-thiadiazoles
4. Crystal data for 2a: C8H6N3F3S2 M = 265.27 Triclinic space group. P (No. 2) a = 7.715 (3) b = 15.594 (5) c = 15.598 (4) Å V = 1582.3 (1.0) Å Z = 6 (3 molecules per an asymmetric unit) Dc= 1.67 gcm−1 μ = 2.7 cm−1. Yellowish green crystals of 2a were obtained from hexane/cyclohexane solution. A crystal of dimensions 1.12 × 0.65 × 0.25 mm was sealed in a glass capillary. Measurements were made on an Enraf‐Nonius CAD 4 diffractometer at room temperature with a graphite monochromator and MoKα radiation. The intensities of 4153 reflections were measured (0 ≤ h ≤ 8 ‐16 ≤ k ≤ 16 ‐16 ≤ 1 ≤ 16) by using the ω/2θ scan technique to θmax= 45°. The structure was solved by direct methods and refined by least‐square methods. Final agreement factors R = 0.053 Rw = 0.077. Atomic scattering factors were taken from International Tables for X‐ray Crystallography Vol. IV 1974. All calculations and drawings were performed using a Micro VAX II computer with the SDP system.
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