Article Dans Une Revue European Journal of Organic Chemistry Année : 2020

Mild Deprotection of Dithioacetals by TMSCl/NaI Association in CH3CN

Résumé

A mild process using a combination of TMSCl and NaI in acetonitrile is used to regenerate carbonyl compounds from a variety of dithiane and dithiolane derivatives. This easy to handle and inexpensive protocol is also efficient to deprotect oxygenated and mixed acetals as 1,3-dioxanes, 1,3-dioxolanes and 1,3-oxathianes quantitatively. As a possible extension of this method, it was also showed that nitrogenated-substrates as hydrazones, N-tosylhydrazones and ketimes reacted well under these conditions to give the expected ketones in high yields. The methodology proposed herein is a good alternative to the existing methods since it does not use metals, oxidants, reducing agents, acidic or basic media, and keto-products were obtained in high to excellent yields.

Fichier principal
Vignette du fichier
Manuscrit EJOC hal.pdf (537.11 Ko) Télécharger le fichier
Origine Fichiers produits par l'(les) auteur(s)
Licence
Loading...

Dates et versions

hal-02910296 , version 1 (01-08-2020)

Licence

Identifiants

Citer

Yunxin Yao, Guangkuan Zhao, Abdallah Hamze, Mouad Alami, Olivier Provot. Mild Deprotection of Dithioacetals by TMSCl/NaI Association in CH3CN. European Journal of Organic Chemistry, In press, ⟨10.1002/ejoc.202000979⟩. ⟨hal-02910296⟩
263 Consultations
969 Téléchargements

Altmetric

Partager

  • More