70388-86-2Relevant academic research and scientific papers
Base-Catalyzed Transesterification of Thionoesters
Newton, Josiah J.,Britton, Robert,Friesen, Chadron M.
, p. 12784 - 12792 (2018/10/20)
Here we report a convenient synthesis of thionoesters by base-catalyzed transesterification. Benzyl and alkyl thionobenzoates and thionoheterobenzoates were efficiently prepared using various alcohols catalyzed by the corresponding sodium alkoxide. This methodology features a broad substrate scope, good to excellent yields, short reaction times, while simultaneously driving the reaction toward completion through the removal of the methanol byproduct. We also report the conversion of a small collection of thionobenzoates into the corresponding α,α-difluorobenzyl ethers to demonstrate the conversion of alcohols into difluorobenzyl or difluoroheterobenzyl ethers, a process that could prove useful for lead optimization in medicinal chemistry.
Stereochemical Studies on Hemiorthothiol and Hemiorthothiolate Tetrahedral Intermediates
Khouri, Farid F.,Kaloustian, Moses K.
, p. 6683 - 6695 (2007/10/02)
This study deals with hemiorthothiol-RC(OR')2SH-tetrahedral intermediates including (a) two acyclic ones of type , (b) two types of monocyclics and , and (c) four bicyclic systems , , , and .The breakdown of (R = Ph, R' = Et) led to thiono esters 34 and 35; that of (R = Me, Ph) resulted in hydroxy thiono esters 36-39, whereas the cleavage of (R =Me, Et) yielded thionolactones 49-53 and hydroxy thiono esters 55-58.The study of rigid bicyclic intermediates - helped uncover the role of stereoelectronic effects in the breakdown of hemiorthothiol tetrahedral intermediates.Finally, a family of isolable hemiorthothiolate tetrahedral intermediates-RC(OR')2S-+Na-viz. ->--> (monocyclic) and -> (bicyclic) is reported.
