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• 142-29-0 cyclopentene 
• 882-33-7 diphenyldisulfane 
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• 14376-81-9 trans-1,2-dichorocyclopentane 

Relevant academic research and scientific papers

Convenient method for the addition of disulfides to alkenes

Catalytic disulfenylation reaction of alkenes by common Lewis acids has been investigated in detail. While reactions by FeCl3 were feasible with cycloalkenes and other simple alkenes, much faster and excellent conversions were possible by AlCl

Metal cation-exchanged montmorillonite-catalyzed addition of organic disulfides to alkenes

The addition of organic disulfides to alkenes, giving vic-bis(alkylthio) alkanes and vic-bis(arylthio)alkanes, proceeds in chlorobenzene in the presence of a catalytic amount of a variety of metal cation-exchanged montmorillonites (abbreviated as Mn+

Disulfidation of Alkynes and Alkenes with Gallium Trichloride

(Matrix presented) Treatment of diphenyl disulfide and terminal alkynes with gallium trichloride afforded (E)-1,2-diphenylthio-1-alkenes selectively (E/Z > 20/1). Alkenes also underwent this reaction to form trans adducts.

Mono- and bisadducts from the addition of thianthrene cation radical salts to cycloalkenes and alkenes

Thianthrene cation radical salts, Th.+ X-(X- = a, ClO4-; b, PF6-; c, SbF6-), add to cycloalkenes (C5-C8) in acetonitrile (MeCN) to form 1,2-bis(5-thianthreniumyl)cycloalkane salts and 1,2-(5,10-thianthreniumdiyl)cycloalkane salts, most of which have now been isolated and characterized. These are called bis- (3, 6, 9, 12) and monoadducts (4, 7, 10, 13). The proportional amount of the monoadduct obtained in the initial stage of the reaction varied with the cycloalkene in the order C6 ? C5 7 ? C8. Thus, the ratio bis:mono for C5 and C7 was, respectively, about 80/20 and 50/50. In contrast, only about 5% of the C6 monoadduct (7a) and none of 7b, c was obtained, while for C8 none of the bisadducts 12a-c was found. Bisadducts 3 and 9 lost thianthrene (Th) slowly in MeCN solution and changed into monoadducts 4 and 10. A comparable change from 6a into 7a was not observed. The monoadducts, themselves, lost a proton slowly in dry MeCN and opened into 1-(5-thianthreniumyl)cycloalkenes (5, 8, 11, 14). With 3 and 9, particularly, it was possible to follow with NMR spectroscopy the succession of changes, for example, 3 to 4 to 5. The opening of a monoadduct was made faster by adding a small amount of water to the solution. The bisadducts of 4-methylcyclohexene (15a) and 1,5- cyclooctadiene (17a) were isolated and characterized. Although a small amount of monodduct (16a) of 4-methylcyclohexene was found with NMR spectroscopy, it could not be isolated. Bis- and monoadducts were obtained also in additions of Th.+ ClO4- to acyclic alkenes, in relative amounts that, again, varied with the alkene. From cis-2-butene the dominant product was the bisadduct (18), while the monoaduct (19) was characterized with NMR spectroscopy but could not be isolated. In contrast, trans-3-hexene gave mainly the monoadduct (21), while the bis adduct (20) could not be isolated. With 4-methyl-cis-2-pentene, both bis- (22) and monoadduct (23) were isolated, the former being dominant. The conversion of 18 into 19 was characterized with NMR spectroscopy. In all cycloalkene bisadducts, the configurational relationship of the two thianthrenium groups was trans, while in the monoadducts, the bonds to the single thianthrene dication were (necessarily) cis. In both bis- and monoadducts of acyclic alkenes, the configuration of the alkene was retained. The mechanisms of addition with retention of configuration, of conversion of a bis- into a monoadduct, and of opening of a monoadduct are discussed. Products were identified with a combination of NMR spectroscopy, X-ray crystallography, elemental analysis, and (for cycloalkene adducts) reaction with thiophenoxide ion.

1,2-Disulphenylation of Alkenes Induces by a Hypervalent Iodine(III) Reagent

Addition of diphenyl disulphide and dimethyl disulphide to alkenes successfully proceeded with to give high yields of 1,2-bis(phenylthio)alkanes and 1,2-bis(methylthio)alkanes, respectively.