Synthesis of 1-Deuterioalkyl Halides from Cyclic S-Alkylsulfonium Salts and Heavy Water

✍ Scribed by Dr. H. Dorn

• Book ID: 101548317
• Publisher: John Wiley and Sons
• Year: 1967
• Tongue: English
• Weight: 128 KB
• Volume: 6
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.196703711

✦ Synopsis

The IR spectrum of ( I ) , measured in the NaCl and KBr regions, shows strong bands at 1287 (vS=N), 1189(vS=N), (VaSC-F), 1135 (vsC-F) 736 (v,,S-F) (vsC-F) 736 (v,,S-F), and 665 cm-1 (v,S-F). The IgF-NMR spectrum contains two signals, at -59.8 ppm ( S F 3 and 51.9 ppm (CF3S), referred to CC13F as external standard. The mass spectrum shows, besides the molecule ion at m/e = 185, typical fragments CF3SN-SF (m/e 166), CF3SN (115), SNS (78), and SN (46) as well as other peaks.

Product ( I ) is also formed, along with other products, on reaction of CF3SNCO with SF4 In a 300 ml steel autoclave at 100°C and 15 atm. Compound (2) boils at 77'C/80 mm and melts at -58'C. Its IR spectrum contains two very intense bands at 1171 and 1105 cm-1. Absorptions of medium intensity occur at 940, 753, 650, 503, and 464 cm-1. The chemical shift of the 19F signal is at 52.39 ppm (CI3CF as external standard). Typical fragments CFjSNSNS (m/e 193), CF3SNS (147), SNS (78), CF3 (69), SN (46), and S (32) appear in the mass spectrum along with the molecular ion at mje = 262.