Dialkyl Disulfides Research Articles

ChemInform Abstract: ELECTRON IMPACT INDUCED PROCESSES OF THERMALLY AND PHOTOCHEMICALLY LABILE ORGANIC SULFUR COMPOUNDS. A MASS SPECTRAL STUDY OF DIALKYL THIOSULFONATES, DISULFIDES, TRISULFIDES, AND ALPHA‐DISULFONES

Chemischer InformationsdienstVolume 6, Issue 52 Physical Organic Chemistry ChemInform Abstract: ELECTRON IMPACT INDUCED PROCESSES OF THERMALLY AND PHOTOCHEMICALLY LABILE ORGANIC SULFUR COMPOUNDS. A MASS SPECTRAL STUDY OF DIALKYL THIOSULFONATES, DISULFIDES, TRISULFIDES, AND ALPHA-DISULFONES E. BLOCK, E. BLOCKSearch for more papers by this authorM. D. BENTLEY, M. D. BENTLEYSearch for more papers by this authorF. A. DAVIS, F. A. DAVISSearch for more papers by this authorI. B. DOUGLASS, I. B. DOUGLASSSearch for more papers by this authorJ. A. LACADIE, J. A. LACADIESearch for more papers by this author E. BLOCK, E. BLOCKSearch for more papers by this authorM. D. BENTLEY, M. D. BENTLEYSearch for more papers by this authorF. A. DAVIS, F. A. DAVISSearch for more papers by this authorI. B. DOUGLASS, I. B. DOUGLASSSearch for more papers by this authorJ. A. LACADIE, J. A. LACADIESearch for more papers by this author First published: December 30, 1975 https://doi.org/10.1002/chin.197552046Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume6, Issue52December 30, 1975 RelatedInformation

Normal vibrations and molecular conformations of dialkyl disulfides

Normal coordinate calculations were carried out for the following dialkyl disulfides: dimethyl, t-butyl methyl, di- t-butyl, ethyl methyl and diethyl. Modified Urey—Bradley force constants were refined by the method of least squares to give best agreement with the observed frequencies. The functional dependence of the normal frequencies on the dihedral angles about the SS and CS bonds was calculated. It was found that the SS stretching frequency varies little with the dihedral angle about the SS bond but shows a definite dependence on the dihedral angles about the CS bonds. The latter results from a weak coupling of the SS stretching mode with the CCS bending modes. The present study confirms the correlation between the SS stretching frequency and the conformation about the CS bonds recently proposed by Sugeta, Go and Miyazawa.

Kinetics of the Thermal Decompositions of Diaryl and Dialkyl Disulfides

Abstract A kinetic study of the thermal decomposition of diphenyl disulfide, its p-methoxy, p-methyl, and p-chloro derivatives, and di-n-butyl and di-t-butyl disulfides in tetralin was made. The rate of decomposition was followed by the decrease of disulfide and the spontaneous first-order rate constants for these disulfides at 196, 207, and 217 °C and the activation parameters were obtained. It was observed that the rates of the decompositions for diaryl disulfides are increased by p-substituents (CH3O>Cl\simeqCH3>H) and that that of di-t-butyl disulfide is comparable to diaryl disulfides, whereas, di-n-butyl disulfide shows no decomposition under these conditions. A reaction scheme of the decomposition including induced decomposition is proposed from the kinetic results and product analysis. Moreover, the properties of a thiyl radical in relation to the above results are discussed from the electronic and ESR spectra of the aryl thiyl radicals generated from the photolysis of corresponding thiols in a glass of 2-methyltetrahydrofuran at −196 °C.

Reactions of tertiary arsine oxides with mercaptans

The reaction of tertiary arsine oxides with mercaptans is an oxidation-reduction reaction and leads to the formation of the corresponding tertiary arsines and dialkyl(diaryl) disulfides.

ジ-<i>n</i>-プロピルポリスルフィドおよびこれらのモノスルホキシド合成

In general, monosulfoxides of di-alkyl disulfides have characteristic odor and some antibacterial activity, for instance, allicin extracted from garlic Allium sativum has strong odor and antibacterial activity but less stability. Di-n-propyl disulfide, di-n-propyl trisulfide, and di-n-propyl tetrasulfide were synthesized, oxidized to monosulfoxides by perbenzoic acid, and their chemical structures speculated by UV, IR spectra and moleculer refraction. They showed some antibacterial activity and more stability than allicin.

Vibrational Spectra and Molecular Conformations of Dialkyl Disulfides

Abstract The infrared and Raman spectra of several dialkyl disulfides were measured and their conformations were discussed in relation with the characteristic S–S and C–S stretching vibrations. The infrared spectra in the solid state and the temperature dependence of Raman spectra were measured for ethyl methyl disulfide and diethyl disulfide. For ethyl methyl disulfide, the gauche-gauche isomer was more stable than the trans-gauche isomer by about 0.9 kcal/mol while for diethyl disulfide the gauche-gauche-gauche isomer was more stable than the trans-gauche-gauche isomer by about 0.6 kcal/mol in the liquid state. Only the gauche-gauche form for ethyl methyl disulfide and only the gauche-gauche-gauche form for diethyl disulfide were observed in the solid state.

Photosensitized oxidation of dialkyl disulfides

Photosensitized oxidation of dialkyl disulfides

Cogwheel effect in dialkyl disulfides

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTCogwheel effect in dialkyl disulfidesBengt Nelander and Stig SunnerCite this: J. Am. Chem. Soc. 1972, 94, 10, 3576–3577Publication Date (Print):May 1, 1972Publication History Published online1 May 2002Published inissue 1 May 1972https://doi.org/10.1021/ja00765a053RIGHTS & PERMISSIONSArticle Views109Altmetric-Citations19LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (259 KB) Get e-Alerts Get e-Alerts

The Reaction of Diaryl Disulfides with the Cyanide Ion

Abstract The reaction of symmetrical disulfides with the cyanide ion in various solvents has been investigated. The reaction modes may be summarized as follows: (1) Dialkyl disulfides and diaryl disulfides with electron-with-drawing substituents react with the cyanide ion in DMSO or DMF to give the corresponding monosulfides. (2) Diaryl disulfides with electron-donating substituents react with DMSO to yield aryl methyl sulfides. (3) Diaryl disulfides are cleaved by the cyanide ion into thiolate anions and aryl thiocyanates, which then react with alcohol to afford alkyl aryl sulfides.

S–S AND C–S STRETCHING VIBRATIONS AND MOLECULAR CONFORMATIONS OF DIALKYL DISULFIDES AND CYSTINE

Abstract Raman and infrared spectra of dialkyl disulfides were measured. Correlations of S–S and C–S stretching frequencies to molecular conformations were found for dialkyl disulfides.The molecular structure of cystine in aqueous solution was studied on the basis of the observed S–S and C–S stretching vibrations.

Formation of dialkylthiophenes by thermolysis of di(1‐alkenyl) disulfides and alkyl 1‐propenyl disulfides

Abstract3,4‐Dialkylthiophenes are formed in good yields by heating di(1‐alkenyl) disulfides at 150‐200° in the presence of potassium hydrogen sulfate. Thermolysis of alkyl 1‐propenyl disulfides gives mixtures of sulfur‐containing compounds, consisting mainly of 3,4‐dimethylthiophene, dialkyl disulfide, alkyl and 1‐alkenyl monosulfides, and dialkyl trisulfide.

Synthesis of 3,5-dialkyl-1,2,4-trithiolanes: Assignment of configuration and conformational analysis by PMR

3,5-Dialkyl-1,2,4-trithiolanes (I–IV) have been synthesized in reasonable yields by a new route ▪ involving chlorination of dialkyl disulfides to α-chloroalkyl sulfenyl chlorides, reaction with potassium iodide giving di-α-chloroalkyl disulfides and subsequent cyclization with sodium sulfide. All dialkyltrithiolanes synthesized exist in two isomeric configurations ( cis/trans), separable by preparative GLC or column chromatography over alumina. We were able to assign unequivocally the cis and trans configurations by use of the Nuclear Overhauser Effect. From the temperature dependence of the PMR spectra and from Aromatic Solvent Induced Shifts in the spectra it appeared that all dialkyltrithiolanes show pseudorotation: the relative abundance of each conformer is dependent on the bulk of the alkyl groups. The energy barrier for pseudorotation was estimated to be smaller than 6 kcal/mole.

New variation of the alkaline cleavage of dialkyl disulfides

1. Diisobutyl disulfide at a temperature of 210–220°, in the presence of catalytic amounts of KOH or Na2S2, is almost quantitatively cleaved with the formation of isobutanethiol (80–97%), hydrogen sulfide and isobutylene. 2. In the presence of catalytic amounts of the base, cleavage practically does not occur at a temperature of 170–180° and lower.

Alkylthiolation of ambident anions derived from some unsaturated organic sulfides

AbstractReaction of the anions derived from 1,1‐bis(alkylthio)‐2‐alkynes RCCCH(SC2H5)2 (R = alkyl, vinyl or phenyl) with dialkyl disulfides R′SSR′ or alkyl alkanethiosulfonates R′SSO2R′ gives 1,1,3‐tris(alkylthio)‐1,2‐alkadienes RC(SR′) = C = C(SC2H5)2 in good yields. Alkylthiolation of CH3SC ≡ CC(SC2H5)2 with CH3SSCH3 affords (CH3S)2C = C = C(SC2H5)2. The 1‐alkynyl sulfides C2H5C≡CSC2H5 and CH3C≡CSCH3 have been converted into CH3C(SC2H5)=C=C(SC2H5)2 and (CH3S)2C = C=C(SCH3)2, respectively by reaction with alkali metal amide in liquid ammonia and dialkyl disulfide. The latter compound dimerises on heating. Tris(alkylthio)allenes R″CH2C(SR′)=C=C(SC2H5)2 isomerise to the conjugated dienes R″CH=C(SR′)‐CH=C(SC2H5)2 when heated in the presence of acids. Ethylthiolation of the anions of R′CH2C(R″)=C(SC2H5)2 (R″ = H or CH3; R′ = H, CH3 or SC2H5) gives predominantly R′CH=C(R″)‐C(SC2H5)3 as isolable products.

Interaction of acetylene with organic disulfides

Dialkyl disulfides are added to acetylene, forming 1,2-bis(alkyithio)ethenes and vinylalkyl sulfides.

Synthesis of bisalkylxanthogen trisulfides [O,O-dialkyl trithiobis(thioformates)

1. A new method is proposed for the preparation of bisalkylxanthogen trisulfides by heating the corresponding disulfides with sulfur in a boiling water bath. 2. Under these conditions dialkyl disulfides do not react with sulfur. 3. Nine bisalkylxanthogen trisulfides and eight bisalkylxanthogen disulfides were synthesized; of these,bisoctylxanthogen and bisnonylxanthogen disulfides have not been described previously.

Possible Effect of Charge Transfer Complexation on the Dihedral Angle of Dialkyl Disulfides

<b>Possible Effect of Charge Transfer Complexation on the Dihedral Angle of Dialkyl Disulfides</b>

A Systematic Study of the Photolysis of Some Dialkyl Disulfides in a Rigid Glass at 77 degrees K.

A Systematic Study of the Photolysis of Some Dialkyl Disulfides in a Rigid Glass at 77 degrees K.

Equilibrium Studies on the Disproportionation Reaction between Some Dialkyl Disulfides.

Equilibrium Studies on the Disproportionation Reaction between Some Dialkyl Disulfides.

The Reaction of Triethyl Phosphite with a Dialkyl Disulfide

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Reaction of Triethyl Phosphite with a Dialkyl DisulfideHerbert I. Jacobson, Ronald G. Harvey, and Elwood V. JensenCite this: J. Am. Chem. Soc. 1955, 77, 22, 6064–6065Publication Date (Print):November 1, 1955Publication History Published online1 May 2002Published inissue 1 November 1955https://doi.org/10.1021/ja01627a085RIGHTS & PERMISSIONSArticle Views198Altmetric-Citations23LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (270 KB) Get e-Alerts Get e-Alerts