Capturing elusive alkenyl radicals in the Wharton reaction and its interrupted cyclization.

Kornkamon Akkarasereenon, Yichen Liu, Yin Tung Lai, Rongbiao Tong

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Article in Chemical science, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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4 authors.

Kornkamon AkkarasereenonDepartment of Chemistry, The Hong Kong University of Science and Technology Clearwater Bay Kowloon Hong Kong China rtong@ust.hk +86 23581594 +86 23587357.

Yichen LiuDepartment of Chemistry, The Hong Kong University of Science and Technology Clearwater Bay Kowloon Hong Kong China rtong@ust.hk +86 23581594 +86 23587357.

Yin Tung LaiDepartment of Chemistry, The Hong Kong University of Science and Technology Clearwater Bay Kowloon Hong Kong China rtong@ust.hk +86 23581594 +86 23587357.

Rongbiao TongDepartment of Chemistry, The Hong Kong University of Science and Technology Clearwater Bay Kowloon Hong Kong China rtong@ust.hk +86 23581594 +86 23587357.ORCID https://orcid.org/0000-0002-2740-5222

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6 · The paper itself

Abstract

The Wharton reaction is a widely used transformation in organic synthesis, enabling the conversion of α,β-epoxy ketones into versatile allylic alcohols. Despite its discovery more than 60 years ago, the detailed mechanism has remained elusive and controversial. While the prevailing mechanism involves the intermediate of an alkenyl anion, several sporadic reports have challenged this pathway, instead suggesting the involvement of an alkenyl radical. Yet no direct evidence has been provided for either species. Herein, we report the first direct capture of the elusive alkenyl radical intermediate in the Wharton reaction using well-established radical traps, including TEMPO (a persistent radical scavenger), PhSSPh, Me

Identifiers

PMID42039792

DOI10.1039/d6sc01519k

PMCPMC13108335

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