ArticleThe Journal of organic chemistry2018
Pot-Economy Autooxidative Condensation of 2-Aryl-2-lithio-1,3-dithianes.
Article in The Journal of organic chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Synthesis of Unsymmetrical Ketones Using Chelation-Controlled Sequential Substitution ofACS omega · 2022Article
- Efficient Copper-Catalyzed Highly Stereoselective Synthesis of Unprotected C-Acyl Manno-, Rhamno- and Lyxopyranosides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Functionalized Cyclopentenes via the Formal [4+1] Cycloaddition of Photogenerated Siloxycarbenes from Acyl Silanes.The Journal of organic chemistry · 2022Article
- Recent application of visible-light induced radicals in C-S bond formation.RSC advances · 2020Review
- Article
- Reactions of 2-Aryl-1,3-Dithianes and [1.1.1]Propellane.Angewandte Chemie (International ed. in English) · 2019Article
Corrections and comments
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The autoxidative condensation of 2-aryl-2-lithio-1,3-dithianes is here reported. Treatment of 2-aryl-1,3-dithianes with n-BuLi in the absence of any electrophile leads to condensation of three molecules of 1,3-dithianes and formation of highly functionalized α-thioether ketones orthothioesters in 51-89% yields upon air exposure. The method was further expanded to benzaldehyde dithioacetals, affording corresponding orthothioesters and α-thioether ketones in 48-97% yields. The experimental results combined with density functional theory studies support a mechanism triggered by the autoxidation of 2-aryl-2-lithio-1,3-dithianes to yield a highly reactive thioester that undergoes condensation with two other molecules of 2-aryl-2-lithio-1,3-dithiane.
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Registered trials
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