Synthesis and characterization of novel organic heteroatom compounds from reaction of Woollins' reagent with various organic substrates

GRAPHICAL ABSTRACT

ABSTRACT

A series of new selenium-containing heteroatom compounds were synthesized in good yields by the reaction of Woollins’ reagent with various organic substrates such as cyclohexylamine, N-benzoylbenzamide, benzoic anhydride, 4-fluoro-N-(2-oxo-2-phenylethyl)benzamide, N-benzoylbenzamide, benzoic anhydride, 3-(bromomethyl)benzonitrile, 1,2-diphenylethane-1,2-diol, and sodium alcoholate. Three representative X-ray structures are described.

Keywords:

• Woollins’ reagent
• benzamides
• diselenoperoxyanhydrides
• heteroatom compounds
• single crystal structures

Acknowledgments

We are grateful to the University of St Andrews for financial support and the EPSRC National Mass Spectrometry Service Centre (Swansea) for mass spectral measurements.

Notes

a Single crystal structure of (6): Yellow prism crystal 0.120 × 0.120 × 0.030 mm, C₁₆H₁₂N₂Se₂, M = 390.20, monoclinic, space group P2₁/n, a = 8.723(3), b = 8.258(2), c = 20.888(7) Å, α = 90°, β = 99.221(10)°, γ = 90°, V = 1485.2(8) ų, Z = 4, ρ_calcd = 1.745 g cm⁻³, μ = 49.701 cm⁻¹, 9275 reflections collected, 2689 unique [R_(int) = 0.0314], R₁ = 0.0344, wR₂ = 0.0769. CCDC 1054712.

b Single crystal structure of (8): Red needle crystal 0.100 × 0.020 × 0.010 mm, C₁₄H₁₄SeTe₂, M = 516.42, orthorhombic, space group Pbcn, a = 32.991(14), b = 7. 223(3), c = 6.083(3) Å, α = 90°, β = 90°, γ = 90°, V = 1449.6(11) ų, Z = 4, ρ_calcd = 2.366 g cm⁻³, μ = 65.132 cm⁻¹, 6774 reflections collected, 1306 unique [R_(int) = 0.0978], R₁ = 0.0584, wR₂ = 0.1507. CCDC 1054713.

c Single crystal structure of (17): Colorless chunk crystal 0.210 × 0.110 × 0.070 mm, C₁₈H₂₁NPSe, M = 361.30, monoclinic, space group C2/c, a = 17.178(8), b = 10.958(5), c = 18.744(11) Å, α = 90°, β = 98.37(3)°, γ = 90°, V = 3491(3) ų, Z = 8, ρ_calcd = 1.375 g cm⁻³, μ = 22.371 cm⁻¹, 14,083 reflections collected, 3049 unique [R_(int) = 0.1317], R₁ = 0.0747, wR₂ = 0.2569. CCDC 1054714.

Figure 3. Single crystal structure of compound (13). Selected bond lengths (Å) and angles (å): Se(1)-P(1) 2.139(3), P(1)-N(1) 1.672(7), P(1)-C(1) 1.839(9), P(1)-C(7) 1.819(9); Se(1)-P(1)-N(1) 119.6(3), Se(1)-P(1)-C(1) 1115(3), Se(1)-P(1)-C(7) 112.4(3), N(1)-P(1)-C(1) 104.6(4), N(1)-P(1)-C(7) 102.3(4), C(1)-P(1)-C(7) 105.0(4).