Investigation of thia-Diels-Alder Reactions by Ultrafast Transient Absorption Spectroscopy and DFT Calculations.

ABSTRACT: The thia-Diels-Alder reaction represents a versatile synthetic method for the preparation of six-membered sulfur-containing compounds. However, the mechanism of the thia-Diels-Alder reactions remains unclear. In this work, time-resolved spectroscopic experiments and DFT calculations demonstrate that phenacyl sulfide undergoes Norrish II cleavage to produce thioaldehyde, and ortho-hydroxy benzhydryl alcohol occurs in a dehydration reaction to generate o-QMs using diphenylphosphate as the catalyst. Then, the thia-Diels-Alder reaction takes place between thioaldehyde and o-QMs by an asynchronous concerted mechanism. The illustration of the thia-Diels-Alder reaction mechanism not only provides important support for organic synthesis and drug design but

SUBMITTER: Yin D 

PROVIDER: S-EPMC10976361 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature