Organo-catalyzed photoelectrochemical ring-contraction of arylidenecyclobutanols via radical cation-triggered semipinacol rearrangement.

ABSTRACT: The semipinacol rearrangement has proven to be an efficient strategy for converting allylic alcohols into carbonyl compounds bearing an α-quaternary carbon center. Traditionally, this semipinacol rearrangement is initiated through two primary modes, namely electrophile and radical-triggered pathways. Notably, these two strategies predominantly lead to ring-expansion β-functionalized products from cyclic allylic alcohols. In contrast, the radical cation, possessing carbon-centered radical and electrophilic carbocation dual reactivity, potentially triggers ring contraction semipinacol rearrangement of cyclic allylic alcohols, but remains underexplored. This is presumably due to the favorable C-C bond cleavage facilitated by ring-strain release and the challenge associated with overcoming the

SUBMITTER: Zheng Y 

PROVIDER: S-EPMC12679509 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature