A kind of preparation method and application of benzophosphaphthalene derivative
A technology of derivatives, benzophosphine, applied in the field of preparation of organic compounds, can solve the problems of difficulty in obtaining raw materials, harsh reaction conditions, complicated operation, etc., and achieves short reaction time, easy availability of raw materials, and simple reaction operation and post-treatment process. Effect
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Embodiment 1
[0049] Example 1: Synthesis of 1-(naphthalene-1-yl)-3-phenylbenzo[de]phosphanaphthalene-1-oxide
[0050] Using phenylacetylene and dinaphthylphosphine oxide as raw materials, the reaction steps are as follows:
[0051] Add phenylacetylene (0.051 g, 0.5 mmol), dinaphthylphosphine (0.30 g, 1 mmol), CuI 2 (0.032g, 0.1 mmol), phenyl isopropyl hydroperoxide (0.23 g, 1.5 mmol), and ethyl acetate (2 mL), 60 o C reaction;
[0052] TLC tracking reaction until complete completion;
[0053] The crude product obtained after the reaction was separated by column chromatography (ethyl acetate:petroleum ether=1:1) to obtain the target product (yield 96%). Based on the E44 epoxy resin and dicyandiamide system, the flame retardant properties of the above products were studied according to the national standard. The oxygen index of E44 / dicyandiamide and E44 / dicyandiamide / product (12wt% added) were 24 and 27 respectively. The analytical data of the product are as follows: 1 H NMR (400 ...
Embodiment 2
[0054] Example 2: Synthesis of 1-(naphthalene-1-yl)-3-(4-tolyl)benzo[de]phosphanaphthalene-1-oxide
[0055] With 4-methylphenylacetylene and dinaphthyl phosphine as raw materials, the reaction steps are as follows:
[0056] Add 4-methylphenylacetylene (0.053 g, 0.5 mmol), dinaphthylphosphine (0.30 g, 1 mmol), CuI (0.019 g, 0.1 mmol), phenylisopropyl hydroperoxide (0.46 g, 3 mmol), and water (2 mL), 100 o C reaction;
[0057] TLC tracking reaction until complete completion;
[0058] The crude product obtained after the reaction was separated by column chromatography (ethyl acetate: petroleum ether = 1:1) to obtain the target product (yield 85%). The analytical data of the product are as follows: 1 H NMR (400 MHz, CDCl 3 ): δ 8.51 (m, 1H), 8.35(m, 1H), 8.17 (d, J = 8.3 Hz, 1H), 8.11 (m, 1H), 8.04 (d, J = 7.7 Hz, 2H), 7.89 (d, J = 8.3 Hz, 1H), 7.72 (d, J = 7.4 Hz, 1H), 7.68 – 7.54 (m, 4H), 7.51– 7.30 (m, 3H), 7.05 (m, 2H), 6.58 (d, J = 9.8 Hz, 1H), 2.44 (s, 3H).
Embodiment 3
[0059] Example 3: Synthesis of 1-(naphthalene-1-yl)-3-(4-methoxyphenyl)benzo[de]phosphanaphthalene-1-oxide
[0060] Using 4-methoxyphenylacetylene and dinaphthyl phosphine as raw materials, the reaction steps are as follows:
[0061] Add 4-methoxyphenylacetylene (0.066 g, 0.5 mmol), dinaphthylphosphine (0.30 g, 1 mmol), Cu(SCN) into the reaction flask 2 (0.0179 g, 0.1 mmol), tert-butanol peroxide (0.45 mL, 3 mmol) and 1,2-dichloroethane (2 mL), 80 o C reaction;
[0062] TLC tracking reaction until complete completion;
[0063] The crude product obtained after the reaction was separated by column chromatography (ethyl acetate:petroleum ether=1:1) to obtain the target product (yield 79%). The analytical data of the product are as follows: 1 H NMR (400 MHz, CDCl 3 ): δ 8.31 (m, 1H), 8.21– 8.05 (m, 2H), 8.02 (d, J = 8.3 Hz, 2H), 7.86 (d, J = 8.1 Hz, 1H), 7.72 (d, J = 7.4 Hz, 1H), 7.60 (m, 3H), 7.46 – 7.32 (m, 3H), 7.24 (m, 2H), 6.96 (d, J = 8.5 Hz, 2H), 6.56 (d, ...
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