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By Willemse J. A.

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Extra resources for Carbon Monoxide as Reagent in the Formulation of Aromatic Compounds

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16). If however, the basicity of both reagents is assumed to fall in close proximity of each other and excess acid is used, the protonation of both CO and the aromatic substrate is a definite probability and the reaction should be governed by the presence and position of protonation equilibria. e. some un-protonated molecules are available to act as nucleophiles and thus allowing the reaction to proceed. 20). 16), might prevail during these reactions, it only holds true if it is assumed that CO is the more basic of all reactants employed.

C 50 208 45 12 p-Hydroxybenz-ald. 1% 8 9 10 11 a Toluene (386) Toluene (271) Anisole (231) Phenol (266) un-activated, b 5 5 5 5 activated at 150°C for 2h in argon, c calcined at 500°C for 50h in air In an effort to reduce the Brønsted acidity and increase the Lewis acidity, water was removed from the catalyst at 150°C. This catalyst also did not promote formylation (Run 3). These results raised the question whether the material used showed any catalytic activity. A literature procedure213 for acylation using benzoic acid anhydride failed (Run 5), which suggests that it may still contain small amounts of moisture, not removed during the activation step.

5: Attempted CO formylation and acylation of aromatics using sulphated zirconiumoxide as catalyst. 5 - Toluene (336) a 80 - 100 15 - b 80 - 100 20 - 20 Toluene (333) 20 4 Toluene (292) a 2 - Aceticanhydride (25) - 100 3 - 5 Toluene (141) 1 c - Benzoicanhydride (4) - 100 3 - 6 Toluene (141) 1 c - Benzoicanhydride (4) - 100 3 o-, m-, p-Mebenzophenone, benzoic acid 7 Toluene (271) 3c 50 - 45 12 - Anisole (231) c 50 - 45 12 - c 50 44 45 12 p-Toluald. 1% c 50 263 45 12 Phenol, no ald. c 50 208 45 12 p-Hydroxybenz-ald.

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Carbon Monoxide as Reagent in the Formulation of Aromatic Compounds by Willemse J. A.


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