Propane-1,3-dithiol

With excess base the dianion is formed, which is easily oxidized by electron transfer or reaction with 02  

Reduction of the disulfide product also occurs via an ECE process that is facilitated by the presence of H30+  

For the latter system, the primary electrochemistry is reduction of H30+ to an H- atom, which is stabilized via formation of an S—H bond. Such a process is closely similar to the biological reduction of disulfides via H-atom transfer from NADH/flavoproteins. 

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Stable structures are best supported by chelating dithiolate ligands. The monodentate PhS- ligand gives some analogous compounds, but they have proved less stable throughout repeated catalytic cycles. The dithiols from which the chelates used in these studies have been derived are 2-(mercaptomethyl)thiophenol, 1,2-ethane dithiol and 1,3-propane dithiol. 

Scheme 9.9 The attachment of thiobutylisothioisocyanante linker and its removal with propane dithiol (the bottom part of the scheme).

Lithium aluminum hydride reduced )J-azidoethylbenzene to j8-aminoethyl-benzene in 89% yield [600], The azido group was also reduced with aluminum amalgam (yields 71-86%) [149], with titanium trichloride (yields 54-83%) [601], with vanadous chloride (yields 70-95%) [217] Procedure 40, p. 215), with hydrogen sulfide (yield 90%) [247], with sodium hydrosulfite (yield 90%) [259], with hydrogen bromide in acetic acid (yields 84-97%) [232], and with 1,3-propanedithiol (yields 84-100%) [602]. Unsaturated azides were reduced to unsaturated amines with aluminum amalgam [149] and with 1,3-propane-dithiol [602]. 

An efficient double conjugate addition of ethane and propane dithiols in the presence of sodium methoxide to propargylic carbonyl compounds (127) has been developed. The corresponding amino-substituted propargylic aldehydes afforded piperidine derivatives.182... 

When the substrate is a dithiol (e.g., propane dithiol, HSCH2CH2CH2SH), it undergoes an apparent reversible oxidation at a gold electrode 19... 

There are two candidates for this dreadful smell—propane dithiol (called acetone gem-dithiol above) or 4-methyl-4 Sulfanylpentan-2-one. It is unlikely that anyone else will be brave enough to resolve the controversy. 

Steiner141 has also prepared heterocyclic derivatives in which a seven- or eight-membered ring is fused to the 3,4-position of the 1,2-benzothiazine molecule. Thus, reaction of ester 199 with 1,2-ethanedithiol, 1,3-propane-dithiol, or ethanolamine gave 215,216, or 217, respectively. Similarly reaction of 199 with 2-mercaptophenol, 1,2-benzenedithiol, or o-aminophenol gave... 

Double Michael addition. In the presence of MgO alky ny 1 ketones and 1,3-propane-dithiol react to afford 2-acylmethyl-l,3-dithianes. ... 

Interesting chemistry has been observed in the process of attaching pendant donors and propylene chloride substituents to arsenic-sulfur heterocycles <85CB2714>. The arsine oxide (84) was converted into the heterocycle (85) by reaction with 1,3-propane dithiol in the presence of potassium hydroxide. Deprotonation of this compound with LDA at — 50 °C to — 35 C afforded the 2-lithio intermediate... 

The dithiolate cofactor has been proposed to be SCH2NHCH2S [15], although protein crystallography cannot distinguish between N, O, and C. 1,3-Propane-dithiol is unknown biologically, so despite its routine chemical character, this species is no more plausible as the cofactor than the hetero-substituted derivatives. 

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