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• 498-66-8 norborn-2-ene 

Relevant academic research and scientific papers

Synthesis, characterization, mechanism of decomposition, and antiproliferative activity of a class of PEGylated benzopolysulfanes structurally similar to the natural product varacin

Benzopolysulfanes, 4-CH3(OCH2CH2) 3NHC(O)-C6H4-1,2-Sx (x = 3-7 and 9) were synthesized with a PEG group attached through an amide bond and examined for water solubility, antitumo

Diselenide-assisted sulfuration of dienes

Various diselenides assist in the sulfuration of dienes giving cyclic di- and tetrasulfides as main products. The reaction requires a 2-fold excess of diselenides to be efficient. Catalytic amounts of diselenides result in lower yields. This is likely due to secondary reactions (polymerization, aromatization) occurring during extended reaction times under catalytic conditions. It was verified that the sulfur-transferring properties of diselenatetrasulfides are virtually identical to those of diselenides combined with sulfur. Contrary to previous claims, not only the cyclic diselenatetrasulfide but also linear diselenatetrasulfides (RSeSnSeR) transfer sulfur to dienes. A mechanism is proposed and its implications to the nature of diatomic sulfur are discussed.

Oxidation of tetrathiolanes: Isolation of a vic-disulfoxide, 5-(1-adamantyl)-5-tert-butyltetrathiolane 2,3-dioxide and its decomposition to the dithiirane 1-oxide and 'S2O'

Oxidation of 5-(1-adamantyl)-5-tert-butyltetrathiolane (3a) with dimethyldioxirane (DMD) at -78 or -20°C gave (1R*,3S*)-and (1R*,3R*)-3-(1-adamantyl)-3-tert-butyldithiirane 1-oxides (cis-4a and trans-4a, respectively) as the final products. The reaction was revealed to proceed through stepwise oxidation to the corresponding 2-oxide and then to the 2,3-dioxide 5, a vic-disulfoxide; the latter is isolated in pure form by low-temperature recrystallization and is fairly stable at room temperature in the crystalline state. The structure of 5 was determined by X-ray crystallography. The 2,3-oxide 5 decomposes in solution above -10°C to cis-4a, trans-4a, and 'S2O' as the principal products. The reactive sulfur species, S2O, is trapped by 2,3-dimethyl-1,3-butadiene to give 4,5-dimethyl-3H,6H-1,2-dithiin 1-oxide. In the absence of the diene, S2O disproportionates to SO2 and 'S3', which is trapped by norbornene to give exo-norbornane trithiolane (exo-3,4,5-trithiatricyclo[5.2.1.02,6]decane).

New route to 2-cyanobenzimidazoles

N-Monosubstituted 1,2-diaminobenzenes 4 (R = Me, Ph, PhCH2, and 3,4- Me2C6H3CH2) react with 4,5-dichloro-1,2,3-dithiazolium chloride 1 in dichloromethane at room temperature to give the corresponding 2- cyanobenzimidazoles 6. If pyridine is added at the beginning of the reaction, the intermediate imino-1,2,3-dithiazoles 5 can be isolated. Upon thermolysis, most of the imines 5 give the 2-cyanobenzimidazoles 6 in fair to good yields. 1.2-Diaminobenzene can be converted in high yield into the mono-imine 5i or the bis-imine 12, R = H; thermolysis of 5i gives 2-cyanobenzimidazole in high yield. Conversion of 5 into 6 involves the loss of both sulfur atoms and with the N-phenylimino derivative 5b singlet diatomic sulfur, S2, has been intercepted with norbornene and with 2.3-diphenylbutadiene to give the expected cycloadducts 7 and 8.

REACTION OF ELEMENTAL SULFUR WITH ACRYLONITRILE. SYNTHESIS OF 1,7-DICYANO-3,4,5-TRITHIAHEPTANE

Reaction of acrylonitrile with elemental sulfur, catalysed by ammoniain dimrthylformamide at 80 grad C results in 1,7-dicyano-3,4,5-trithiaheptane.Spectral data of this new derivative of acrylonitrile are included.