Molecules 2001, 6, M229

Molecules 2001, 6, M229

4-Phenyl-2,2'-bis(phenylsulfonyl)butane

F. Matloubi Moghaddam and O. Khakshoor

Sharif.University of Technology, Department of Chemistry, P.O.Box 11365-9516 Tehran, Iran. E-mail: [email protected]

Received: 16 February 2001 / Accepted: 15 May 2001 / Published: 25 May 2001

During our investigation of the chemistry of bis-gemdiphenylsulphinyl and sulfonyls [1], we have prepared the 4-phenyl-2,2'-bis (phenylsulfonyl)butane from the corresponding thioketal by dimethyldioxirane oxidation [2]. Procedure of synthesis: To a stirring solution of thioketal (I) 0.7 g. (2 mmol) in dry acetone (40 mL) at -78^oC, a solution of dimethyldioxirane 85 mL (0.043 mmol /mL acetone) were added dropwise. Then, the reaction mixture was stirred to reach the room temperature. After evaporation of the solvent under vacuum, the residue was chromatographed on a silica gel column eluting with a mixture of CHCl₃: AcOEt: petroleumether (30:5:65) to yield 0.72 g. (87%) of the compound (II) as white crystals.

Mp.: 132-134 ^oC

IR (KBr pellet): 3061, 1584, 1453, 1307(O=S=O), 1146(O=S=O), 750, 730, 700 cm^-1.

¹H-NMR (CDCl₃, 80MHz): d 1.67(s, 3H), 2.2-2.6(m, 2H), 2.6-3.0(m, 2H), 7.2-8.1(m, 15H).

MS (EI), (formula: C₂₂H₂₂S₂O₄, M.W: 414.1), m/x (%): 414(8.5), 310(3.4), 274(6.8), 273(34), 272(25), 255(3.4), 206(4.3), 141(7), 130(20), 125(35), 115(11.4), 91(100), 77(47).

References

1. Khakshoor, O. M.Sc. Thesis, Sharif University of Technology, Department of Chemistry. 2000.
2. Curi, D.; Pardini, V. L.; Harden, D. B. Heteroatom Chemistry. 1994, 5(5/6), 555.

Sample Availability: Available from the authors and from MDPI.