利用楚加耶夫反應的原理將一級硝基烷與醛肟轉換為腈類化合物

Abstract

腈類化合物在有機化學領域中已被廣泛地應用，不僅可作為合成天然物、藥物、染料或高分子材料的關鍵步驟中的中間化合物；同時，腈類官能基也存在於許多的天然物的結構中。因此，化學家對腈類化合物已進行廣泛地研究。 本論文的研究目的在利用楚加耶夫反應的原理，在室溫的條件下，以二氯甲烷為溶劑，使用二硫化碳、烯丙基溴(或甲基碘)與DBU，將一級硝基烷轉換為腈類化合物，並經由純化後的產物來推測反應進行時的可能反應機構。 因此，綜合上述敘述，本論文呈現此反應具有操作簡單、反應時間短、高效率及高產率來製備腈類化合物的特色。Nitrile compounds have been widely utilized in the synthetic organic chemistry. It is the key intermediate for generating amides, amines, ketones, esters, or carboxylic acids. It is also present many natural products and synthetic compounds which exhibits variety of biological activities. Hence, developing rapid and simple method for the synthesis of nitriles compounds in one pot is an important research topic in the present scenario. A facile route for the synthesis of nitrile compounds by functional group transformation has been developed in this project. This newly development method is based on the Chugaev reaction where the primary nitroalkane can transformed into nitrile compound by the treatment of carbon disulfide, allyl bromide(or iodomethane), and DBU in dichloromethane at room temperature. This synthetic methodology is highly efficient and simply operation with high yield in short time. Furthermore, the plausible mechanistic route was proposed based on literature reports and different controlled experiments.