Synthesis of [4]Dendralene Derivatives Possessing Quadruple 1,3-Dithiol-2-ylidenes and Transformation to a Trimethylenecylopentene in an Oxidation State
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Abstract
New derivatives of [4]dendralene with redox-active 1,3-dithiol-2-ylidene units were synthesized. X-ray crystal structure analysis of the dibenzo-tetramethyl derivative revealed that the molecule takes a conformation in which two vinyl-extended TTF moieties are significantly inclined to each other. The octamethyl derivative underwent cyclization with skeletal rearrangement in the dicationic state to give the corresponding dicationic trimethylenecylopentene, which exhibited a simultaneous two-electron reduction wave at a significantly negative potential of −0.42 V (V vs Fc/Fc+).
合成了具有氧化还原活性的1,3-二硫醇-2-二烷基基的[4]树烯衍生物。对二苯并四甲基衍生物的x射线晶体结构分析表明，该分子具有两个乙烯基延伸的TTF片段明显相互倾斜的构象。八甲基衍生物在指示状态下进行环化和骨架重排，得到相应的指示三亚甲基环戊烯，其同时表现出负电位为- 0.42 V （V vs Fc/Fc+）的双电子还原波。
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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