Ring-closing C-O/C-O metathesis of ethers with primary aliphatic alcohols.

ABSTRACT: In canonical organic chemistry textbooks, the widely adopted mechanism for the classic transetherifications between ethers and alcohols starts with the activation of the ether in order to weaken the C-O bond, followed by the nucleophilic attack by the alcohol hydroxy group, resulting in a net C-O/O-H σ-bond metathesis. In this manuscript, our experimental and computational investigation of a Re₂O₇ mediated ring-closing transetherification challenges the fundamental tenets of the traditional transetherification mechanism. Instead of ether activation, the alternative activation of the hydroxy group followed by nucleophilic attack of ether is realized by commercially available Re₂O₇ through the formation of perrhenate ester intermediate in hexafluor

SUBMITTER: Liu H 

PROVIDER: S-EPMC10076310 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature