Highly Efficient, and Fast Solid State Deprotection of 1,3-Dithianes and 1,3-Dithiolanes using Mercury(II) Nitrate Trihydrate

Abstract

A variety of 1,3-dithianes and 1,3-dithiolanes are deprotected in the solid state to the corresponding parent carbonyl compounds in excellent yields using mercury(II) nitrate trihydrate in a mild, efficient and fast method.

2,2′-Ethylenebis(1,3-dithiane) as a polydentate μ2-, μ4- and μ5-assembling ligand for the construction of sulphur-rich Cu(i), Hg(ii) and heterometallic Cu(i)/Hg(ii) coordination polymers featuring uncommon network architectures

“…46–48 For example, a protocol allowing the efficient and fast deprotection of cyclic thioacetals by Hg(NO 3 ) 2 even in the solid state has been described. 49…”

“…[46][47][48] For example, a protocol allowing the efficient and fast deprotection of cyclic thioacetals by Hg(NO 3 ) 2 even in the solid state has been described. 49 On the other hand, an IR spectroscopic investigation dating from the sixties indicated formations of tetrahedral adducts HgX 2 S 2 through the equatorial donation of a sulphur lone-pair of 1,3-dithiane. According to this study, the mercury-sulphur bond varies in strength in the order Cl > Br > I.…”

Synthesis and characterization of [chloro{2(1H)-pyridinethione-S}{tris(pyridin-2-ylthiolato)methyl-C,N,N′,N″]}nickel(II)], [Ni(TPTM)(SPyH)Cl]

“…Removal of the protecting groups to give back the carbonyl compound has also well been reported, with a variety of conditions being used [24], including the use of different acid and metal salt catalysts. Among the metal salts reported to catalyse dethioketalization reactions are copper salts [25], mercury salts [26], iron salts [27] and bismuth salts [28,29]. The formation of thioacetals and thioketals from their components and the removal of the thiols to give back carbonyl compounds are reversible reactions; for example, metal salts, such as bismuth triflate [28] and nitrate [24], are able to catalyse the formation of thioacetals and thioketals as well as their decomposition.…”

Oxidative Degradation of Thermosets Based on Thioketal Cleavable Linkages in Aqueous Environment

“…Toward developing economic and eco-friendly degradation strategies, thioacetal/thioketal function groups have attracted our attention, which are widely used to protect carbonyl compounds in the organic synthesis to produce 1,3-dithiane and 1,3-dithiolane derivatives . Recently, the dithioacetal/ketal bond has been considered an optimum functional cleavable group that is responsive to degradation by free radical species like reactive oxygen species (ROS) in living systems. , This inspired the researchers to synthesize different thioketal and thioacetal cross-linkers as versatile biomedical application tools. , To the best of our knowledge, the thioketal cross-linker has not been investigated in the development of degradable thermoset materials.…”