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本文报导几种具有不同取代基的芳基丁炔醇的合成和苯基丁炔醇在不同催化条件下的反应性能。通过格氏反应,制得了六种炔醇,其中有三种文献上尚未报导。苯基丁炔醇在H_3PO_4-HCOOH催化下,可转变成苯基丙烯基酮和苄基乙烯基酮。当用HgSO_4-H_2SO_4催化时,只生成苯基丙烯基酮产物,如果所用的HgSO_4-H_2SO_4浓度很稀时,炔醇直接水合成酮醇。所有生成物均可通过分子内的Friedel-Crafts反应而闭合成环状化合物。炔醇及其水化产物和环化产物的光谱数据符合拟定的结构。这些结构的验证,特别是羰基所在位置的确定,能为多环化合物的合成提供某些有用的信息。
This paper reports the synthesis of several aryl-substituted alkynols with different substituents and the reaction performance of phenyl-butyn-1-ol under different catalytic conditions. Six kinds of acetylenic alcohols have been made by Grignard reaction, of which three have not yet been reported. Phenylbutynol in H_3PO_4-HCOOH catalysis, can be converted into phenyl propenyl ketone and benzyl vinyl ketone. When catalyzed by HgSO_4-H_2SO_4, only the phenylpropenyl ketone product is formed. If the HgSO_4-H_2SO_4 concentration used is very dilute, the acetylenic alcohol hydrates directly to the ketol. All products can be closed by intramolecular Friedel-Crafts reaction into a cyclic compound. Spectral data for the acetylenic alcohols and their hydration products and cyclization products are in accordance with the proposed structure. The verification of these structures, especially the location of carbonyl groups, can provide some useful information for the synthesis of polycyclic compounds.