4-Chlorobenzyl sulfide

Bis-(4-chlorobenzyl) sulfide is obtained in 85.7 % yield analogously from 4-chlorobenzyl chloride.290... 

Mitchell has reported that benzyl a-chlorobenzyl sulfides are cleanly converted into stilbenes on successive treatment with PPhs and Bu OK (Scheme 13). Desulfurization of an intermediate thiirane by PPh3 is a likely pathway for this reaction. Benzyl a,a-dichlorobenzyl sulfides are converted into diphe-nylacetylenes under the same conditions." Viehe has reported that pyrolysis of ot-halo-a-alkylthio esters, ketones and nitriles under reduced pressure furnishes a,p-unsaturated esters, ketones and nitriles respectively it is probable that these reactions also take place via intermediate thiiranes. a-Chlorophenacyl phenacyl sulfide is converted into ( )-dibenzoylethylene on treatment with EtsN. ... 

Uses. There may be some captive use of carbonyl sulfide for production of certain thiocarbamate herbicides (qv). One patent (38) describes the reaction of diethylamine with carbonyl sulfide to form a thiocarbamate salt which is then alkylated with 4-chlorobenzyl halide to produce 5- (4- chi o r o b enzyl) A/, A/-diethyl thiocarbamate [28249-77-6], ie, benthiocarb [28249-77-6]. Carbonyl sulfide is also reported to be useful for the preparation of aliphatic polyureas. In these preparations, potassium thiocyanate and sulfuric acid are used to first generate carbonyl sulfide, COS, which then reacts with a diamine ... 

By employing furazans bearing reactive groups attached at both 3- and 4-positions bicyclic derivatives may be constructed. For instance the furazanothiophene (85) and diazepine (93) are obtained by treatment of di(a-chlorobenzyl)- and diamino-furazans with sodium sulfide and ethyl acetoacetate, respectively (77H(6)1173, 78KGS1196). Further examples are described in Section 4.22.3.4. 

The woik of Tuleen and Stevens on the regioselectivity of chlorination of a series of unsymmetrically substituted dialkyl sulfides with NCS provides clues to Ae directive effects implicit in the mechanisms encompassed by Scheme 3. These observations are collected in Scheme 6 where the preferred site of chlorination in each case is indicated with an arrow, the number over the arrow indicating the majortminor product ratio (minor = 1). In the first example, chlorination of benzyl methyl sulfide (2) produces chlorobenzyl methyl sulfide exclusively. Secondly, chlorination of benzyl ethyl sulfide (3) and benzyl isopropyl sulfide (4) also shows a marked, though not exclusive, preference for the benzylic position. In the latter case the extent of benzylic chlorination can be modulated by ring substitution. The directive effects in these internal competitions for p-methyl and p-chloro substituents are correlated by the Hammett relationship with a value of p = 1.0, which is consistent with a mechanism involving abstraction of the more acidic proton in the chlorosulfonium ion intermediate. Further indications of the im-... 

Pradhan, N.C., and M. M. Sharma, Kinetics of Reactions of Benzyl Chloride/ -Chlorobenzyl Chloride with Sodium Sulfide Phase-Transfer Catalysis and the Role of the Omega Phase, Ind. Eng. Chem. Res., 29, 1103 (1990). 

However, conditions foracaricidal action are aalso satisfied by those derivatives in which the two phenyl groups are linked directly or through the insertion of a methylene group by a bivalent sulfur atom. 2,4,4 5-TetrachIorodiphenyl sulfide (tetrasul, 20), 4-chlorobenzyl-4-chlorophenyl sulfide (chlorbenside, 21) and the... 

CMorbenside. l-Chtoro-4-[[(4-chlorophenyi)-methyl]thu>]benzene p-chiorobenzyl p-chlorophenyl sulfide chlorocide Chlorparacide Chlorsulphadde Mitox. C13H -QjS mol wt 269.20. C 58.00%, H 3.74%, Cl 26.34%, S 11.91%. Prepn of analogous compd, p-chlorobenzyl p-ni-trobenzyl sulfide, from p-chlorophenylthiol and p-nitroben -zyl chloride Stevenson et at. Brit, pat, 738,170 (1955 to Boots Pure Drug). Chemical and biological properties C ran ham et al., Chem. Ind. (London) 1953, 1206. 

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