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- Title
Sodium Arenesulfinates‐Involved Sulfinate Synthesis Revisited: Improved Synthesis and Revised Reaction Mechanism.
- Authors
Ji, Yuan‐Zhao; Li, Hui‐Jing; Zhang, Jin‐Yu; Wu, Yan‐Chao
- Abstract
Reaction of alcohols with sodium arenesulfinates could afford either sulfones or sulfinates, and O‐attack of sulfinate anions onto the in situ generated carbocation intermediates from alcohols was the previous proposed reaction mechanism in many syntheses of sulfinates. This concept, which is often used consciously or unconsciously, was revised herein by using isotopic labeling experiments and development of an improved sulfinate synthesis. The improved sulfinate synthetic protocol possesses many advantages such as a high sulfinate/sulfone selectivity, a broad substrate scope, metal‐free, and mild reaction conditions. The revised reaction mechanism necessitates revision of many previous proposed reaction mechanisms in literatures. Reaction of alcohols with sodium arenesulfinates could afford either sulfones or sulfinates, and O‐attack of sulfinate anions onto in situ generated carbocation intermediates from alcohols was the previous proposed mechanism in many syntheses of sulfinates. This concept, which is often used consciously or unconsciously, was revised herein by using isotopic labeling experiments and development of an improved sulfinate synthesis.
- Subjects
SULFINATES; REACTION mechanisms (Chemistry); CARBOCATIONS; CHEMICAL reactions; RADIOLABELING
- Publication
European Journal of Organic Chemistry, 2019, Vol 2019, Issue 8, p1846
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201900097