Cyanoazulene-based Multistage Redox Systems Prepared from Vinylcydopropanecarbonitrile and Cyclopentenone via Divinylcyclopropane-rearrangement Approach

摘要

A series of 4-cyanoazulene derivatives 1-5 were synthesized from 4-cyanohexahydroazulen-l-one, which was efficiently obtained by the annulation of the seven-membered ring on the cyclopentenone skeleton via the divinylcyclopropane rearrangement. This synthetic protocol is also effective in preparing 1,1'-bi(4-cyanoazulene) (6) and its p-phenylene-extended derivative 7, which undergo multistage redox reactions exhibiting electrochemical amphotericity.