Diethyl sulphide

Diethyl sulphide 0.025M Bu4NOH MeOH PrOH H20(2 2 l) -1.78... 

Benzyne is thought to interact with simple ethers such as diethyl ether to form zwitter-ions. However, simple products analogous to those obtained with for example diethyl sulphide have not been detected 1). Apparently the more basic ether, 1,2-dimethoxyethane is cleaved by benzyne 130>. 

Diethyl sulphide [352-93-2] M 90.2, m 0°/15mm, 90.1°/760mm, d 0.837, n 1.443. Washed with aq 5% NaOH, then water, dried with CaCl2 and distd from sodium. Can also be dried with MgSO4 or silica gel. Alternative purification is via the Hg(II) chloride complex [(Et)2S.2HgCl2] (see dimethyl sulphide). 

In the dehalogenation of 4-chlorobiphenyl, 1-chloro- and 1-bromonaphthalene, 9-chloro- and 9-bromoanthracene and 4-chlorobenzonitrile, diethyl sulphide has been used as electron donor397. The involvement of radical anions in these reactions is evidenced by the incorporation of deuterium into the products when the reactions were performed in acetonitrile-deuterium oxide. Lithium diisopropylamide in hexane or tetrahydrofuran398 and sodium methyl siliconate (MeSi03Na3)399 have also been used as electron transfer reagents in the photodehalogenation of 4-chlorobiphenyl. 

If the residues of mdthomyl , an insecticide commonly used in viticulture, are present in the must they can lead to the formation of methanethiol, ethanethiol, diethyl sulphide and diethyl disulphide. If these compounds are present in wine they can give it cooked cauliflower or wet wool aromas. 

The combustion of diethyl sulphide proceeds explosively at 170 °C whereas at 155 °C the reaction is very quickly self-inhibited. Analytical studies using a packed vessel at 195 °C showed that the products were sulphur dioxide, acetaldehyde, acetic acid and water [110]. 

Diphenyl sulphoxide, thiodiglycol sulphoxide, and diethyl sulphoxide are oxidised to the corresponding sulphones. Howard and Levitt studied the kinetics of oxidation of these compounds at pH 8 in a phosphate buffer (aqueous solution) and found the rates to be first-order with respect to peroxodisulphate and independent of the substrate concentration over the limited range employed (0.01-0.02 M). The removal of oxygen had no effect on the rate. Diethyl sulphide is oxidised very rapidly initially, then at the same rate as diethyl sulphoxide. Howard and Levitt concluded that the sulphide is first oxidised to the sulphoxide which in turn is oxidised to the sulphone, but Wilmarth and Haim point out that this interpretation cannot be correct, and conclude that the reaction must be more complex. 

The first group of sulphur compounds mentioned above can be defined as common fermentative sulphur volatiles (CFSV) and includes in our presentation ethylmercaptan (EtSH), dimethyl sulphide (DMS), diethyl sulphide (DES), dimethyl disulphide (DMDS), diethyl disulphide (DEDS), methyl thioacetate (MTA), ethyl thioacetate (ETA), 2-mercaptoethanol (ME), 2-(methylthio)-l-ethanol (MTE), 3-(methylthio)-l-propanol (MTP), 4-(methylthio)-l-butanol (MTB), benzothiazole (BT) and 5-(2-hydroxyethyl)-4-methylthiazole (HMT) (see Table 5.6). 

AI3-18785 Bear skunker Diethyl sulfide Diethyl sulphide Diethylsulfid Diethylthioether EINECS 206-526-9 Ethyl monosulfide Ethyl sulfide Ethyl Thioether Ethylthioethane HSDB 5563 NSC 75157 Sulfodor Thioethyl ether UN2375. Used as a bear and animal repellent. Registered by EPA as an animal repellent (cancelled). Liquid mp = -103.9° bp = 92.1° d ° = 0.8362 Xm = 194, 215 nm (e = 4786,1585, C7H16) slightly soluble in H2O, CCI4, soluble in EtOH, EtzO. Fluka. 

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