含氮及磷碳六十衍生物之反應與化學性質探討

Abstract

我們發現當碳六十、烯炔與含磷化合物反應，其結果會隨使用的含磷化合物不同而有不同的反應類型。與烷氧基膦反應，會得到三員環產物及水解產物、五員環水解產物；若使用芳香膦類與碳六十、烯炔反應，則會得到三員環及五員環產物。含氮化合物部分，我們在醋酸鈀催化下合成了五員環及六員環碳六十產物，並以長碳鏈增加其溶解度，嘗試探討碳鏈自五增加到十一對化合物化性的影響。另一部分， 我們探討同富勒烯化合物的開洞反應。

Using organophosphorus compounds and enyne to react with C60, we found that the products are different with organophosphorus compounds. Treatment of phosphites and enyne with C60 afford three corresponding fullerene derivatives, consisting of a phosphite ylide group and a cyclopropane ring on the fullerene, another with a phosphonates and a cyclopropane ring, and last with a phosphonates and a cyclopantane ring. If using aryl phosphines, the products incorporating cyclopropane and cyclopentane rings are obtained. Phosphite ylide reacts with hydrobromic acid to afford phosphine oxide. On the other hand, phosphine ylide reacts with hydrobromic acid to yield a novel compound, having weak hydroxy bond with phosphorus. We charactered these compounds by spectroscopic methods, including NMR, IR and UV. In the other project incorporating nitrogen, the palladium-catalyzed reactions of C60 with anilide and benzamide afford fulleroindolines and fulleroisoquinolinones derivatives, respectively. For increasing the solubility, the compounds incorporate long carbon chains from 5 to 11. In addition, we compare the properties of fulleroindolines and fulleroisoquinolinones derivatives.