Ring-opening reactions of 2-alkoxy-3,4-dihydropyrans with thiols or thiophenols
Minghao Li1, Haoquan Li, Tao Li
1Institute of Physical Chemistry and Industrial Catalysis, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Hongshan District, Wuhan, China.
Abstract:
An electrophilic ring-opening reaction of 2-alkoxy-3,4-dihydropyran with a thiophenol or thiol is developed for the first time. The generated product contains not only a 1,3-dicarbonyl moiety but also a fragment of bis(alkylthio)methane. A possible mechanism is also proposed on the basis of postulating a ring-opening monotransthioacetalization product, which was prepared by using LiBr as catalyst as an intermediate.
More Related Videos
10:12Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Preparation and Reactions of Thiols
Base-Catalyzed Ring-Opening of Epoxides
Preparation and Reactions of Sulfides
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Acid-Catalyzed Ring-Opening of Epoxides
