My PhD dissertation - Institut Fresnel

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1 H NMR: δ = 7.32 (dddd, J = 9, 8, 2, 1, 3 H), 6.89 (ddd, J = 8, 5, 1 Hz, 3 H), 6.83
(t, J = 7 Hz, 3 H), 6.69 (ddd, J = 8, 5, 2 Hz, 3 H), 3.74 (s, 9 H) ppm.
13 C NMR: δ = 161.6 (d, J = 17 Hz), 134.2, 129.9, 124.7 (d, J = 13 Hz), 120.9 (d,
J = 2 Hz), 110.3, 56.1 ppm.
31 P NMR: δ = - 36.8 ppm.
MS: 353 (31%, M + + 1), 84 (100%).
Tris[4-(N,N-dimethylamino)phenyl]phosphine (3): Prepared from 4-bromo-N,N-
dimethylaniline (30 g, 0.15 mol); colorless needles; m.p. 267 - 269 °C (ref. [82] m.p. 265 -
275 °C); yield: 19.5 g (83%).
1 H NMR: δ = 7.28 (symm. m, 6 H), 6.57 (symm. m, 6 H), 2.92 (s, 18 H) ppm.
13 C NMR: δ = 149.7, 131.7 (d, J = 12 Hz), 114.1, 108.7, 40.7 ppm.
31 P NMR: δ = - 128.0 ppm.
MS: 392 (4%, M + ), 137 (100%), 120 (96%).
Tris(1-naphthyl)phosphine (4): Prepared from 1-bromonaphthalene (31 g, 0.15 mol). After
two successive recrystallizations from ethanol, the expected product was obtained as colorless
needles; m.p. 261 - 264 °C (ref. [83] m.p. 261 - 265 °C); yield: 17.8 g (86%).
1 H NMR: δ = 8.3 (m, 3 H), 7.8 (m, 6 H), 7.56 (dd, J = 6.7, 5.4 Hz, 3 H), 7.3 (m,
9 H) ppm.
13 C NMR: δ = 138.2 (d, J = 20 Hz), 133.7 (d, J = 20 Hz), 133.5 (d, J = 3 Hz),
129.9 (s), 128.9 (d, J = 6 Hz), 128.5 (d, J = 2 Hz), 126.0 (d, J = 2 Hz), 125.7 (d,
J = 1 Hz), 125.3 (d, J = 2 Hz), 125.1 (d, J = 3 Hz) ppm.
31 P NMR: δ = -32.4 ppm.