DD214131A1 - PROCESS FOR THE PREPARATION OF 3H, 6H-1,2-DITHIOLO (4,3-C) (1,2) -dithiol-3,6-DITHION - Google Patents

PROCESS FOR THE PREPARATION OF 3H, 6H-1,2-DITHIOLO (4,3-C) (1,2) -dithiol-3,6-DITHION Download PDF

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Publication number
DD214131A1
DD214131A1 DD24871383A DD24871383A DD214131A1 DD 214131 A1 DD214131 A1 DD 214131A1 DD 24871383 A DD24871383 A DD 24871383A DD 24871383 A DD24871383 A DD 24871383A DD 214131 A1 DD214131 A1 DD 214131A1
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DD
German Democratic Republic
Prior art keywords
dithiolo
dithione
dithiol
preparation
sulfur
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Application number
DD24871383A
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German (de)
Inventor
Richter
Fanghaenel
Original Assignee
Tech Hochschule C Schorlemmer
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Application filed by Tech Hochschule C Schorlemmer filed Critical Tech Hochschule C Schorlemmer
Priority to DD24871383A priority Critical patent/DD214131A1/en
Publication of DD214131A1 publication Critical patent/DD214131A1/en

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Abstract

Die Erfindung betrifft ein Verfahren zur Herstellung von 3H,6H-1,2-Dithiolo(4,3-c)(1,2)-dithiol-3,6-dithion.Diese Verbindung ist als Ausgangsprodukt fuer die Synthe weiterer Dithiolo-dithiole, Hetercocyclen, Farbstoffen und Polymeren von Interesse. Die Herstellung geschieht erfindungsgemaess dadurch, dass 2,3-S- oder O-funktionalisierte Butendisaeureester mit Phosphorpentasulfield oder 1,3-Di-p-anjsyl-1,3-diphosha-2,4-dithientan-1,3-dithion, ggf. in Gegenwart von Schwefel, in einem Loesungsmittel wie Toluen, Xylen, Chlorbenzen oder Methoxybenzen umgesetzt werden.The invention relates to a process for the preparation of 3H, 6H-1,2-dithiolo (4,3-c) (1,2) -dithiol-3,6-dithione.This compound is as starting material for the synthesis of other dithiolo-dithiols , Heterocycles, dyes and polymers of interest. The preparation according to the invention is characterized in that 2,3-S- or O-functionalized butenedioic acid esters with phosphorus pentasulfide or 1,3-di-p-anjsyl-1,3-diphosha-2,4-dithientan-1,3-dithione, if necessary in the presence of sulfur, in a solvent such as toluene, xylene, chlorobenzene or methoxybenzene.

Description

Verfahren zur Herstellung von 3H,6H-1,2-Dithiolo 4 ,3-c](1 .2 )-dithiol-3,6~dithionProcess for the preparation of 3H, 6H-1,2-dithiolo 4,3-c] (1, 2) -dithiol-3,6-dithione

Anwendungsgebiet der ErfindungField of application of the invention

Die Erfindung betrifft ein Verfahren zur Herstellung von 3H,6H-1,2-Dithiolo [4,3-c] (1,2)-dithiol-3,6-dithion. Diese Verbindung besitzt Bedeutung für die Synthese weiterer Dithiolo-dithiole, von Heterocyclen, Farbstoffen, 'Polymeren und' organischen Elektronenleitern.The invention relates to a process for the preparation of 3H, 6H-1,2-dithiolo [4,3-c] (1,2) -dithiol-3,6-dithione. This compound is important for the synthesis of other dithiolodithiols, heterocycles, dyes, polymers and organic electron conductors.

Charakteristik der bekannten technischen LösungenCharacteristic of the known technical solutions

Das 3H.6H-1{2-Dithiolo [4 ,3-c] (1,2)-dithiol-3,6-dithion ist eine bislang nicht beschriebene Verbindung«The 3H.6H-1 { 2-dithiolo [4, 3-c] (1,2) -dithiol-3,6-dithione is a compound not previously described «

Ziel der ErfindungObject of the invention

Ziel der Erfindung ist es, ein Verfahren zur Herstellung von 3E,6H-1,2-Dithiolo [4,3-c] (1,2)~dithiol~3,6-dithion aus leicht zugänglichen Ausgangsprodukten zu entwickeln.The aim of the invention is to develop a process for the preparation of 3E, 6H-1,2-dithiolo [4,3-c] (1,2) dithiol-3,6-dithione from readily available starting materials.

Darlegung aes Wesens aer üriinaungPresentation of a being aer üriinaung

Der .Erfindung liegt die Aufgabe zugrunde, 3H,6H-1,2-Dithiolo Γ4 ,3-c"] (1 ,2 )-dithiol-3 ,6-dithion in einfacher VJe ise aus leicht zugänglichen Ausgangsprodukten zu synthetisieren, Brfindungs-The object of the invention is to synthesize 3H, 6H-1,2-dithiolo Γ4, 3-c "] (1,2) -dithiol-3,6-dithione in a simple manner from readily available starting products.

fllllfllll J J ,.,_,,., _,

gemäß wird diese Aufgabe dadurch gelöst, daß Butendisäureester bzw, deren C-Y-H-Tautomere (wenn R"" und/oder R1 V/asse: stoff ist), der Formel IAccording to this object is achieved in that Butendisäureester or whose CYH tautomers (when R "" and / or R 1 V / acse: is material), the formula I.

wobei R , R^, R"5, R^ Alkyl, Aralkyl, Ar:/1; R „ R' auße Wasserstoff; und X, Y Sauerstoff oder Schwefel sein kann, mit einem Schwefelungsmittel wie Phosphorpentasulfid oder 1,3-Dip-anis^l-1,3-diphospha-2,4-dithietan-1,3-dithion, ggf. in Gegenwart von Schwefel, in einem organischen Lösungsmittel,, wia Toluen, !Lvlen, Chlorbenzen oder Methos^bensen im üJenperaturbereich von 100 ° - 180 0C, vorzugsweise zwischen 140 ° -wherein R, R 1, R " 5 , R 1, C 1 alkyl, aralkyl, Ar: / 1, R" R 'may be hydrogen and X, Y may be oxygen or sulfur, with a sulfurizing agent such as phosphorus pentasulfide or 1,3-diphenyl Anis ^ l-1,3-diphospha-2,4-dithietane-1,3-dithione, optionally in the presence of sulfur, in an organic solvent, such as toluene, toluene, chlorobenzene or Methos benensen in the üperature range of 100 ° - 180 0 C, preferably between 140 ° -

zu 3H,6H-1,2-Dithiolo[4,3-c] (1,2)-dithiol-3,6-dithionto 3H, 6H-1,2-dithiolo [4,3-c] (1,2) -dithiol-3,6-dithione

160 ° C160 ° C

der Formel i±the formula i ±

Ausführungsbeispieleembodiments

Ausführungsbeispiel 1Embodiment 1

0,01 Giol Butendisäurediester der Formel I werden zusannen miu,004 - 0,04 mol ?hosOhGr~entasulfid und bi0.01 giol butenedioic diester of the formula I will zusun miU, 004 - 0,04 mol? HosOhGr ~ entasulfid and bi

hwefel in 20 bis 60 ml Toluen bis zur Beendisuns: der Bilduns;sulfur in 20 to 60 ml of toluene until completion: of the image;

von Ii (Kontrolle durch Dlmnschichtchromatographie oder 7j_8-Spektroskopie) am Sieden gehalten. ITach dem Abkühlen saugt man ausgeschiedenes Produkt ab und kristallisiert aus einem hochsiedenden Lösungsmittel Um5 oder man reinigt durch ChromatographieIi (control by thin-layer chromatography or 7j_8 spectroscopy) boiled. After cooling, the precipitated product is filtered off with suction and crystallized from a high-boiling solvent Um 5 or purified by chromatography

Ausb.: 15 - 20 % d. Th.; schwarz-grüne Kristalle;Yield: 15 - 20 % d. Th .; black-green crystals;

Pp.: 258 υ0 (Subl. ab ca. 180 UC)Pp .: 258 υ 0 (subl. From approx. 180 U C)

Ausführungsbeispiel 2Embodiment 2

0,01 mol Butendisaureester der Formel I werden zusammen mit 0,004 - 0,04 mol 1 ,3-Di-p-anis:/l-1 ,3-diphospha-2 ,4-diethan-1,3-dithion und bis zu 0,1 mol Schwefel in 20 bis 60 ml Toluen bis zur Beendigung der Bildung von II (Kontrolle durch Dünnschichtchromatographie oder VIS-Spektroskopie) am Sieden gehalten. Man arbeitet dann wie unter Ausführungsbeispiel 1 angegeben auf.0.01 mol of butenedioic esters of the formula I are added together with 0.004-0.04 mol of 1,3-di-p-anis: / 1-1,3-diphospha-2,4-diethane-1,3-dithione and up to 0.1 mol of sulfur in 20 to 60 ml of toluene until the formation of II (control by thin layer chromatography or VIS spectroscopy) is stopped boiling. It then works as indicated in Example 1.

3H,6H-1,2-Dithiolo[4,3-c](1,2)-dithiol-356-dithion3H, 6H-1,2-dithiolo [4,3-c] (1,2) -dithiol-3 5 6-dithione

Bsp.Ex. TT YY R1 =R2 R 1 = R 2 ρΛε4 ρΛε 4 Ausb. ilY. il i Ausf,-bsp»i Ausf, -bsp » -1 - 1 frf\frf \ -- 11 ΛΛ 00 SS HJ. öHJ. ö t-But-Bu 1818 22 22 00 .S.S -Lj ü-Lj ü t-But-Bu 1717 22 00 00 HeHe TTTT 88th IlIl . ', ' 00 00 UJTUJT HH CC

Claims (1)

SrfiridungsansOrucnSrfiridungsansOrucn Verfahren zur Herstellung von 3H,6H-1,2-Dithiolo[4s3-cj(1 ,2 dithiol-3,b-dithion, gekennzeichnet dadurch, daß Butendisäureester der formel IA process for the preparation of 3H, 6H-1,2-dithiolo [4s3-cj (1,2-dithiol-3, b-dithione, characterized in that butenedioic acid ester of formula I YR3 YR 3 1 ' CX1R2 1 'CX 1 R 2 wobei R1, R2, R3, R4 Alkyl, Aralkyl, Aryl; R3, R4 außerdem Wasserstoff; und X, Y Sauerstoff oder schwefel sein kann, mit einem Schwefelungsmittel wie Phosphorpentasulfid oder 1,3-Dip-anisyl-1 ,-3-diphospha-2 ,4-dithietan-1 ,3-dithion, ggf. in Gegenwart von Schwefel, in einem organischen Lösungsmittel, wie Toluen, Xylen, Ghlorbenzen oder Methoxybenzen im Temperaturbereich von 100 - 180 C, vorzugsweise zwischen 140 ° 160 0C zu 3H,6H-1,2-Dithiolo[4,3-c] (1,2)-dithiol-3,6-dithion aer ir'wherein R 1 , R 2 , R 3 , R 4 are alkyl, aralkyl, aryl; R 3 , R 4 also hydrogen; and X, Y may be oxygen or sulfur, with a sulfurizing agent such as phosphorus pentasulfide or 1,3-dip-anisyl-1,3-diphospha-2,4-dithietane-1,3-dithione, optionally in the presence of sulfur, in an organic solvent such as toluene, xylene, or methoxybenzene Ghlorbenzen in the temperature range of 100 - 180 to 3H C., preferably between 140 ° 160 0 C, 6H-1,2-dithiolo [4,3-c] (1,2) dithiol-3,6-dithione aer ir ' S-SS-S f7T t-tj εζ -si A ρ ν·. f7T t-tj εζ -si A ρ ν ·. iJ u vv C_u U Öü *iJ u vv C_u U Öü *
DD24871383A 1983-03-11 1983-03-11 PROCESS FOR THE PREPARATION OF 3H, 6H-1,2-DITHIOLO (4,3-C) (1,2) -dithiol-3,6-DITHION DD214131A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DD24871383A DD214131A1 (en) 1983-03-11 1983-03-11 PROCESS FOR THE PREPARATION OF 3H, 6H-1,2-DITHIOLO (4,3-C) (1,2) -dithiol-3,6-DITHION

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DD24871383A DD214131A1 (en) 1983-03-11 1983-03-11 PROCESS FOR THE PREPARATION OF 3H, 6H-1,2-DITHIOLO (4,3-C) (1,2) -dithiol-3,6-DITHION

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DD214131A1 true DD214131A1 (en) 1984-10-03

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