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Original Articles

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

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Pages 341-346 | Received 18 Mar 2015, Accepted 09 Jul 2015, Published online: 17 Mar 2016
 

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.

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) Å3, Z = 4, ρcalcd = 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) Å3, Z = 4, ρcalcd = 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) Å3, Z = 8, ρcalcd = 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).
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).

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