Direct and mediated electrochemical reductive coupling reactions between alkenes and CO 2 have been studied using an undivided electrochemical cell. Propene and 1-butene were used to study the behavior of monoenes. Propene, in the absence of a mediator, yielded two main products: 2-methyl-butanedioic acid and 3-butenoic acid; from 1-butene, mainly ethenylsuccinic acid and 3-pentenoic acid were generated. As a conjugated diene, 1,3-butadiene was investigated intensively. In the absence of a mediator, 1,3-butadiene was mainly dicarboxylated to give the 1,2-(2-ethenyl-succinic acid) and 1,4-addition product (3-hexene-1,6-dioic acid) and various higher coupling products. Using an NiN3 mediator the reaction between 1,3-butadiene and CO 2 resulted in a preferred generation of the 1,4-addition product: 3-hexene-1,6-dioic acid. Experiments with a Ni-(cyclam) mediator resulted in an increased concomitant generation of a monocarboxylation product: 3-pentenoic acid.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.