Efficient formation of aromatic thiols from thiomethylated precursors

Synthesis and electrochemistry of self-assembled monolayers containing quinone derivatives with varying electronic conjugation

“…The methyl protected thiol has been shown to withstand the conditions needed both for the Pd catalyzed cross coupling reactions and HEW reactions used to create the double and triple bonds [28]. In addition, conditions to generate the free thiol using t-BuSNa as a dealkylation agent have also been reported for a series of thiomethylated compounds without significant contamination by disulfides [29].…”

“…Since t-BuSNa had been reported as a dealkylation agent for both -SCH 3 and -OCH 3 chemical groups [29], we attempted to deprotect both in a single step. In a typical reaction, excess t-BuSNa was reacted with either compounds 1, 2, or 3 in dry DMF at $160°C.…”

Synthesis of triarylphosphines having para –SH and –SMe groups

“…Deprotection of 1 and synthesis of tri-(4-thiophenyl)phosphine (2) In the literature, it has been reported that deprotection of a methylthio group to afford the corresponding thiol can be achieved by reaction of the former with sodium t-butylthiolate in DMF, followed by aqueous HCl [11]. Application of the published protocol to 1, however, afforded a mixture of products in which, according to mass spectral and NMR data, the predominant product is the deprotected phosphinsulfide (4-HSC 6 H 4 ) 3 P@S (Scheme 1).…”

Synthesis and PET evaluation of (R)‐[S‐methyl‐11C]thionisoxetine, a candidate radioligand for imaging brain norepinephrine transporters

“…[31][32][33] However, these reactions failed to proceed cleanly, as previously observed in the particular case of demethylations of some aryl methyl sulfides with sodium thiomethoxide. 34 Aryl sulfides may be protected as their sulfanyl g-propionic acid methyl esters and deprotected by b-elimination under basic conditions. 35 We therefore decided to explore the Michael addition of methyl acrylate to o-hydroxy-thiophenol as the first step in the synthesis of 1.…”