DEVELOPMENT OF NEW SYNTHETIC REACTIONS BY USING THE PROPERTIES OF SELENOCARBONYL GROUP

高效率和选择性的新合成反应的发展是合成有机化学中最重要的问题之一。从起始材料到最终产品的合成过程的加速和减少也是重要的。一种不同的反应方法，使双债券的能力发挥作用，使碳原子变得众所周知。“如果用碳原子来承载较弱的双债券的化合物是设计的和容易处理的，在轧机反应条件下的未预先确定的合成反应将是真实的。”目前的研究的主要目标是探索碳原子和硒原子之间双键高反应的基础上的合成反应，在元素的周期性法表中找到了四个，作为一个结果，使用硒同位素的方法，一个E，硒酰胺提供了新的反应类型，其作用域和限制已被披露为后续。硒同位素对氧化物的添加反应，如E。苯甲酸酯将醛平滑地进行，以给予B-羟基硒酰胺。“硒酰胺在硝酸原子中携带的苯并基组被展示的高立体声电。”使用甲基三氟酯的硒酰胺甲基化在一秒钟内完成，可用于生产硒胺盐。硒胺盐的烷基化可以给α，β-不饱和的酮在高年级中的好。α-硅硒酰胺与醛酸盐的反应，β-不饱和的硒酰胺与E-选择性。这种反应的应用被用于承载长烯烃组的硒酰胺。

The development of new synthetic reactions with high efficiency and selectivity is one of the most important issues in synthetic organic chemistry. The acceleration and reduction of synthetic process from the starting materials to the final products are also of important. A variety of reactions utilizing the ability of double bonds involving the carbon atoms have been known. If the compounds bearing the weak double bonds with the carbon atom are designed and easily handled, unprecedented synthetic reactions under milder reaction conditions for shorter reaction times would be realized. The prime objective of the present research was to explore synthetic reactions on the basis of the higher reactivity of the double bonds between the carbon atom and the selenium atom, which was found in the forth law of the periodic table of elements.As a result, the use of selenium isologues of amides, i.e., selenoamides provided new types of reactions, and their scope and limitations were disclosed as follows.・Addition reaction of selenium isologues of enolate ions, i.e., eneselenolates to aldehydes smoothly proceeded to give b-hydroxy selenoamides. The selenoamides bearing benzyl groups on the nitrogen atom exhibited high stereoselectivity.・Methylation of selenoamides with methyl triflate was complete within one sec to produce selenoiminium salts. The alkynylation of selenoiminium salts took place to give α,β-unsaturated ketones in good to high yields.・The reaction of α-silyl selenoacetamides with aldehydes furnished α,β-unsaturated selenoamdies with E-selectivity. The application of this reaction led to selenoamides bearing long olefinic groups.