O,O'-(丁-2,4-二烯基)桥联联萘酚的串联 RCM-Claisen 重排-[2+2]环加成反应。
Tandem RCM-Claisen rearrangement-[2+2] cycloaddition of O,O'-(but-2-en-1,4-diyl)-bridged binaphthols.
机构信息
Faculty of Chemistry, Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, A-1090 Wien, Austria.
出版信息
Molecules. 2012 Dec 7;17(12):14531-54. doi: 10.3390/molecules171214531.
Abstract
Attempted RCM of 2,2'-bis(allyloxy)-1,1'-binaphthyl resulted in a Claisen-type rearrangement of a postulated labile dioxacyclodecine proceeding at room temperature and followed by [2+2] cycloaddition. Structures of products were confirmed by X-ray crystallography. A mechanistic rationalisation based on relative stabilities of proposed intermediates and transition states is provided.
摘要
尝试对 2,2'-双（烯丙氧基）-1,1'-联萘进行 RCM，导致假定的不稳定二氧杂环十二烷在室温下进行克莱森重排，随后发生[2+2]环加成。通过 X 射线晶体学确证了产物的结构。提供了基于所提出的中间体和过渡态相对稳定性的机理合理化。
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