DIDECYL DISULFIDE

General procedure: NaGeneral procedure: In a round-bottom flask (25 mL) equipped with a condenser, Europhtal (8020) catalyst solution (0.07 mL) was added to amixture of an alkyl halide (2.0 mmol), thiourea (2.2 mmol), H2O(0.1 mL), and NaHCO3 (3.0 mmol) in PEG 200 (1 mL) and themixture was stirred magnetically in an oil bath at 80-90 °C. Thestirring was continued under such conditions up to 2 h after thecomplete consumption of the starting halide. Next, the mixturewas diluted with water (0.5 mL) and extracted with 1:2 n-hexane/EtOAc (3 x 1 mL). The organic layers were decanted, combined, and concentrated to yield the crude product, which wasfurther purified by silica gel chromatography, using n-hexane aseluent.General procedure: CSGeneral procedure: An alkyl halide (2 mmol) and HMDS (3 mmol) were addedto a solution of thiourea (2.2 mmol) in wet DMSO (2 mLDMSO + 0.05 mL H2O). The mixture was stirred magneticallyat 50 °C for 10–24 h. Then, the mixture was dilutedwith water (2 mL) and extracted with 1:1 EtOAc/hexane(3 × 2 mL). The upper layers were decanted, combined, and concentrated. The crude product was purified by silicagel chromatography using low-boiling petroleum ether aseluent to provide the desired disulfide in high yield.General procedure: A mixture of an alkyl halide (2 mmol), thiourea (2.5 mmol), EtGeneral procedure: A mixture of an alkyl halide or alkyl tosylates 1 (2 mmol), thiourea (2.2 mmol), graphene oxide (60 wtpercent), and Na2CO3 (3 mmol) in wet acetonitrile (2 mL CH3CN +0.2 mL H2O) was stirred at 80 C for 3–12 h. The progress of reaction was monitored byTLC using n-hexane. The reaction mixture was then cooled to room temperature and thegraphene oxidewas separated by simple filtration. The filtratewas evaporated under reducedpressure to get the crude product, which was further purified by silica gel chromatographyusing n-hexane as eluent to give disulfide 2 (Table 2). Characterization details of knownproducts, and graphene oxide are provided in the Supplemental Materials.

Molecular Weight:346.7
XLogP3:9.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:19
Exact Mass:346.27279369
Monoisotopic Mass:346.27279369
Topological Polar Surface Area:50.6
Heavy Atom Count:22
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes