烯亚砜化合物的制备及反应概述

An Overview on the Synthesis and Reactions of Sulfines

烯亚砜作为一类重要的反应中间体在有机合成领域发挥着重要应用。常见的烯亚砜制备方法包括:硫羰基化合物氧化、亚磺酰衍生物β-消除反应、改进的Peterson反应、重氮甲基亚砜的杂原子-Wolff重排反应等。作为活性中间体的烯亚砜可以被亲核试剂进攻硫原子中心或者碳原子中心,分别得到亚砜化合物或者新的烯亚砜物种;而其自身亦可以作为亲核试剂,以氧原子作为亲核位点与其他亲电试剂反应。烯亚砜和酰基或者烯基烯亚砜可以分别作为亲双烯体或双烯体发生正常和逆电子需求的Diels-Alder反应。烯亚砜既可以作为亲偶极子,也可以作为偶极子发生偶极环加成反应。此外,烯亚砜自身还可以发生二聚、脱硫等反应。希望本文总结的内容能够对该研究领域感兴趣的化学工作者有所帮助,并促进烯亚砜化学的进一步发展。

Sulfines play an important role as reactive intermediates in organic synthesis.Various methods have been developed for the synthesis of sulfines.These methods can be divided into the oxidation reaction of thiocarbonyl compounds,β-elimination reaction of sulfinyl derivatives,the modified Peterson reaction,hetero-Wolff-rearrangement of diazomethyl sulfoxides and so on.In view of the importance of sulfines,a number of reactions have been developed.Sulfines as reactive intermediates can be attacked on their sulfur atom or carbon atom by nucleophiles to generate sulfoxides or new sulfine compounds,respectively.At the same time,sulfines can also be served as nucleophilic reagents to react with other electrophilic reagents.Furthermore,sulfines as dienophiles and acyl/vinyl sulfines as dienes can take place in normal or inverse electron-demand Diels-Alder reactions to obtain cycloadducts.In addition,sulfines can be employed both as dipolarophiles and dipoles to generate heterocyclic products through dipolar cycloaddition reactions.Furthermore,due to the high activity of sulfines,desulfur and dimerize reactions can happen easily under sunlight or heating conditions.It is hoped that this review article can provide some valuable information for the organic chemists who are interested in the reaction of sulfine compounds and promote the development on the synthesis and application of sulfine compounds.