Diisothiocyanate

Phenylene diisothiocyanate (bitoscanate) [4044-65-9] M 192.3, m 129-131", 130-131", 132". Purified by recrystn from AcOH, pet ether (b 40-60"), Me2CO or aq Me2CO. [van der Kerk et al. Reel Trav Chim Pays-Bas 74 1262 I955 Leiber and Slutkin J Org Chem 27 2214 7962.]... 

Dimethyltin dichloride has a similar chain structure (375). In diethyltin diiodide (374), dimethyltin diisothiocyanate (376, 377), and di-chloro bis(chloromethyl)stannane (378), however, the distorted, trans-RgSnX geometry of each tin atom is completed by two bridging bonds involving the halogen or pseudohalogen atoms on the same, neighboring molecule. 

Heterogeneisation of such dithiourea catalysts was achieved by the synthesis of a series of chiral polythioureas from the corresponding chiral diamine and diisothiocyanate [81]. Results of the catalytic tests have shown that it is important to preserve the C2-symmetry inside the polymeric material [82]... 

See Carbonyl diisothiocyanate, and Dinitrogen tetraoxide, and Hexachlorocyclot-riphosphazine, and Sodium hydride, all below See Perchloric acid Sulfoxides... 

Carbonyl diisothiocyanate [6470-09-3] 0 C(N=C=S)2 Dimethyl sulfoxide See Dimethyl sulfoxide Carbonyl diisothiocyanate See related cyano compounds c3n2os2... 

Phenoxyacetophenone, 46, 94 Phenylacetylene, oxidative coupling to diphenyldiacetylene, 46,39 reaction with sodium hypobiomite to yield phenjdbromoethyne, 46, 86 Phenylacetyl fluoride, 46, 6 Phenylbrojioethyne, 46, 86 l-Phenyl-l,3-hutadiene, 46, 94 Phenyl (-butyl ether, 46, 89 />-Phenylene diisothiocyanate, 45, 21 Phenylethynyllithium 46, 88 Phenylethynymagnesium Grignard reagent, 46, 88... 

Other isothiocyanates obtained by this method are phenyl isothiocyanate (65%), -phenylene diisothiocyanate (71%), p-acetylaminophenyl isothiocyanate (73%), />-ethoxyphenyl isothiocyanate (64%), and -bromophenyl isothiocyanate (55%). 

Diisothiocyanates react with aryl amines to form the 1,3,5-triazine via the thiadiazinone intermediate (88 Scheme 53) (81CB2075). The reaction also works for benzylic amines. 

Base-catalyzed ring-expansion of benzisoxazolones (217) provides a general route to 2,2-dialkyldihydro-l,3-benzoxazin-4-ones (218) (78CPB549) and the 2,4-dione (220) can be prepared by a Beckmann rearrangement of the oxime (219) (02CB3647). 2-Thion-4-ones (222) are formed from salicylic acids (221) by treatment with triphenylphosphine diisothiocyanate in dichloromethane at -40 °C (78CI(L)806). 

In absence of diluent or other effective control of reaction rate, the sulfoxide reacts violently or explosively with the following acetyl chloride, benzenesulfonyl chloride, cyanuric chloride, phosphorus trichloride, phosphoryl chloride, tetrachlorosilane, sulfur dichloride, disulfur dichloride, sulfuryl chloride or thionyl chloride [1]. These violent reactions are explained in terms of exothermic polymerisation of formaldehyde produced under a variety of conditions by interaction of the sulfoxide with reactive halides, acidic or basic reagents [2]. Oxalyl chloride reacts explosively with DMSO at ambient temperature, but controllably in dichloromethane at —60°C [3]. See Carbonyl diisothiocyanate, and Dinitrogen tetraoxide, and Hexachlorocyclo-triphosphazine, and Sodium hydride, all below See Perchloric acid Sulfoxides... 

See Dimethyl sulfoxide Carbonyl diisothiocyanate See related cyano compounds... 

Carbonyl-bis(triphenylphosphine)iridium—silver diperchlorate, 3892 Carbonyl dicyanide, see Oxopropanedinitrile, 1337 Carbonyl difluoride, 0342a Carbonyl diisothiocyanate, 1338 Carbonyl(pentasulfur pentanitrido)molybdenum, 0532 2-Carboxy-3,6-dimethylbenzenediazonium chloride, 3132a Carboxymethyl carbamimoniothioate chloride,... 

Reaction of />-phenylene diisothiocyanate 188 with 7-thiobutyrolactone in an alkaline medium yields a 4-thiocarba-moylthiobutyric acid derivative after acidification. This is cyclized to the 2-thioxo-l,3-thiazepan-4-one derivative 189. The remaining isothiocyanate functionality is subjected to a [2+2] cycloaddition with iVjiV -dicyclohexylcarbo-diimide (DCC) forming a 1,3-thiazetidine system 190 where both isothiocyanate groups have reacted (Scheme 61) <1999JHC1167>. 

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