Rapid and Convenient Synthesis of S-Acetylarenethiols by Non-aqueous Diazotization

Abstract

A series of S-acetylarenethiols were synthesized from aromatic amines by a rapid, convenient and efficient method. Arenediazonium tetrafluoroborates were afforded from aromatic amines, isoamyl nitrite and boron trifluoride etherate in non-aqueous diazotization system, then reacted with potassium thioacetate in dimethylsulfoxide to obtain desired products in moderate to good yields and short reaction times. The product S-acetyl-4-iodothiophenol was characterized by single crystal X-ray diffraction. The crystal belongs to monoclinic, space group P2₁/C with unit cell parameters: a = 0.594 20(12) nm, b = 0.542 00(11) nm, c = 2.9618(6) nm, α = 90.00°, β = 94.23(3)°, γ = 90.00°, D_x = 1.942 g/cm³, Z = 4, F(000) = 528, μ = 3.528 mm^-1, R = 0.039 2, wR = 0.099 3, P = (F_o ² + 2F_c ²)/3, S = 1.077, (Δρ)max = 0.692 × 10³⁰ e/m³, (Δρ)min = -0.558 × 10³⁰ e/m³. The X-ray crystallographic structure (CCDC-684683) clearly shows that the para atoms I and S lie in the benzene ring plane and no hydrogen bonds were observed.