Crystal structure of benzyl (2,6-diisocyano-4-methyl)phenyl ether, C16H12N2O
| Autor: | F. E. Hahn, P. Hein, T. Lügger |
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| Rok vydání: | 1998 |
| Předmět: | |
| Zdroj: | Zeitschrift für Kristallographie - New Crystal Structures. 213:601-602 |
| ISSN: | 2197-4578 1433-7266 |
| Popis: | Source of material: Crystals of the title compound were obtained by recrystallization from CH2Cl2/hexane. The title compound was synthezised by the following sequence: reaction of 4methylhydroxybenzene with fuming nitric acid, reduction of the formed 2,5-dinitro-4-methylhydroxybenzene with hydrazine, conversion of the primary amines into formamide functions by refluxing with phenylformiate in ethanol, protection of the hydroxyl function with benzylbromide and finally conversion of the formamide functions into isocyanides with diphosgene according to the method of Ugi (see ref. 1). The isocyanide formation is not possible with the free hydroxy compound. The overall yield is 25 % based on 4-methylhydroxybenzene. We reported recently on an effective way for the synthesis of Af,(9-heterocarbene complexes using the intramolecular nucleophilic attack of the hydroxy group of coordinated 2-hydroxyphenylisocyanide (see ref. 2). This reaction is reversible and the reaction product depends on the electronic situation at the metal center (see ref. 3). The title compound features two isocyanides, which upon coordination to different metals will compete for the hydroxyl group liberated after 0-benzyl bond cleavage. It will therefore allow for a direct comparison of the carbene formation tendency of two different metal centers under otherwise completely identical reaction conditions. Bond lengths and angles in the compound are normal. The N^C separations in the isocyanide groups of 1.141(3) Â and 1.145 Â Ы1 in the range observed previously for functionalized arylisocyanides (see refs. 4-6). |
| Databáze: | OpenAIRE |
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