The Synthesis of Saturated Cyclic Sulphides

Karaulova, E. N.

doi:10.1070/rc1987v056n06abeh003289

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“…Die photochemische Umsetzung von η 5 -Cp RCo(CO) 2 (Cp R = C 5 H 5 , C 5 H 4 Me, C 5 Me 5 , C 5 -Ph 5 ) (1a -d) mit Thiiran bei niedrigen Temperaturen führt stets zu den dinuklearen µ 2 -1,2-Ethandithiolato-S,S-Komplexen (η 5 -Cp R Co) 2 (µ 2 -S 2 -C 2 H 4 ) (2a -d) (Schema 3a). Daneben lassen sich in Abhängigkeit vom Cp R -Liganden nach aufwendiger säulenchromatographischer Trennarbeit zwei weitere dinukleare Komplexe, das Dimer [η 5 -C 5 H 4 MeCo(µ 2 -S 2 C 2 H 4 ) 2 ] (3b) (Schema 3b) und der Schwefel-verbrückte Komplex [(η 5 -C 5 Ph 5 Co) 2 (µ 2 -S 2 )(µ 2 -S)] (4d) (Schema 3c), isolieren und charakterisieren.…”

Section: Darstellung Und Eigenschaftenunclassified

“…Daneben lassen sich in Abhängigkeit vom Cp R -Liganden nach aufwendiger säulenchromatographischer Trennarbeit zwei weitere dinukleare Komplexe, das Dimer [η 5 -C 5 H 4 MeCo(µ 2 -S 2 C 2 H 4 ) 2 ] (3b) (Schema 3b) und der Schwefel-verbrückte Komplex [(η 5 -C 5 Ph 5 Co) 2 (µ 2 -S 2 )(µ 2 -S)] (4d) (Schema 3c), isolieren und charakterisieren.…”

Section: Darstellung Und Eigenschaftenunclassified

“…µ 2 -Br-Liganden verbrücken relativ symmetrisch die Co-Zentren (Co1-S1 225.3(3) und Co2-S1 225.6(3) pm; Co1-S2 223. [µ 2 …”

Section: Darstellung Und Eigenschaftenunclassified

“…Sie leiten sich formal strukturell von Dihydrobenzvalen ab (Schema 2). In dieser Arbeit werden deshalb photochemische Umsetzungen von η 5 -Cp R Co(CO) 2 Nur Komplex 2a nimmt reversibel SO 2 -Gas unter Bildung von 5a auf; die formale Addition einer Halogenbrücke zwischen beiden Co-Zentren zu 7c gelingt auf Umwegen aus dem neutralen µ 2 -Dibromo-Komplex 6c durch Umsetzung mit 1,2-Ethandithiol.…”

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Photolytisch induzierte Reaktionen von CpCo(CO)₂(Cp = C₅H₅, C₅H₄Me, C₅Me₅ und C₅Ph₅) mit Thiiran zu dinuklearen 1,2-Ethandithiolato-S-S-Komplexen / Photolytically Induced Reactions of CpCo(CO)₂ (Cp = C₅H₅, C₅H₄Me, C₅Me₅ and C₅Ph₅) with Thiirane Yielding Dinuclear 1,2-Ethanedithiolato-S,S Complexes

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Stoll

Nöth

et al. 2006

Zeitschrift Für Naturforschung B

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The complexes CpCo(CO) 2 (Cp = C 5 H 5 , C 5 H 4 Me, C 5 Me 5 and C 5 Ph 5 ) (1a -d) react with thiirane C 2 H 4 S under UV-irridiation in THF to form the dinuclear µ 2 -1,2-ethanedithiolate-S,S complexes [(CpCo) 2 (µ 2 -S 2 C 2 H 4 )] (2a -d) as main products. Using column chromatography, in case of Cp = C 5 H 5 Me also the dimeric complex [C 5 H 4 MeCo(µ 2 -S 2 C 2 H 4 )] 2 (3b), in case of Cp = C 5 Ph 5 the mixed disulfido-sulfido complex [(C 5 Ph 5 Co) 2 (µ 2 -S 2 )(µ 2 -S)] (4d) were isolated in small yields. Only 2a reversibly adds SO 2 gas to form the µ 2 -SO 2 complex [(C 5 H 5 CoSCH 2 ) 2 (µ 2 -SO 2 )] (5a). A bromo ligand bridging the Co atoms can be introduced by the reaction of [(C 5 Me 5 CoBr 2 )] 2 (6c) with 1,2-ethanedithiol which gives the cationic complex [(C 5 Me 5 CoSCH 2 ) 2 (µ 2 -Br)] 2 CoBr 4 (7c). All compounds have been characterized by their IR, 1 H and 13 C NMR and MS spectra and compounds 2b -d, 3b and 7c by X-ray structure analyses, which prove the pseudo tetrahedral skeleton (CpCoS) 2 and the ethane bridge between both sulfur atoms. 3b shows, however, a new unsymmetrical bonding mode of both dithiolato bridges with η 1 -S und µ 2 -S ligand functions.

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Section: Darstellung Und Eigenschaftenunclassified

“…µ 2 -Br-Liganden verbrücken relativ symmetrisch die Co-Zentren (Co1-S1 225.3(3) und Co2-S1 225.6(3) pm; Co1-S2 223. [µ 2 …”

Section: Darstellung Und Eigenschaftenunclassified

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Photolytisch induzierte Reaktionen von CpCo(CO)₂(Cp = C₅H₅, C₅H₄Me, C₅Me₅ und C₅Ph₅) mit Thiiran zu dinuklearen 1,2-Ethandithiolato-S-S-Komplexen / Photolytically Induced Reactions of CpCo(CO)₂ (Cp = C₅H₅, C₅H₄Me, C₅Me₅ and C₅Ph₅) with Thiirane Yielding Dinuclear 1,2-Ethanedithiolato-S,S Complexes

Drobnik

Stoll

Nöth

et al. 2006

Zeitschrift Für Naturforschung B

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ChemInform Abstract: Synthesis of Saturated Cyclic Sulfides

Karaulova¹

1987

ChemInform

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Photochemistry of Thiophen‐2(5H)‐ones

Kiesewetter

Margaretha

1989

Helvetica Chimica Acta

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Dedicated to Prof. Dr. 0. E. Polunsky on the occasion of his 70th birthday (4.XI. 88)Mechanistic evidence for the light-induced ring opening of thiophen-2(5H)-ones 1 in alcohols affording c@-unsaturated mercapto esters 2 is presented. Regio-and stereochemical aspects of the ring closure of alkenylthio (type 3) radicals 15 and 17 to S-heterocycles 16 and 18, of 3-thiahex-5-enyl radicals 4 to (tetrahydrothien-3-yl)methyl radicals 6 and of (2,3-dihydrothien-3-yl)methyl radicals 30 (type 7, but-3-enyl radicals) to cyclopropanemethyl radicals 29 are discussed. Irradiation (A. 350 nm) of 1 in cyclohexane in the presence of 2,3-dimethylbut-2-ene affords [2 + 21 cycloadducts 14 albeit in very low yields.We have recently reported [ 1-71 that on irradiation thiophen-2(5H)-ones 1 behave different from the corresponding 0-heterocycles. While furan-2(5H)-ones exhibit a typical enone-like behaviour yielding cyclodimers, [2 + 21 cycloadducts with alkenes or photoreduction products in alcohols from their triplet state [S] [9], the unsaturated thiolactones 1 undergo ring opening in alcohols to give a$-unsaturated mercapto esters 2 from the excited singlet state. Mercapto esters 2 undergo consecutive light-induced S-H homolysis to afford alkenylthio radicals 3 which in reacting with alkenes or alkynes proved to be useful synthetic intermediates for one-pot syntheses of thiolanes, 2,3-dihydrothiophenes as well as bi-and tricyclic thiolane derivatives via intermediates 4-7 (Scheme 1). Such -Scheme 1

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The Synthesis of Saturated Cyclic Sulphides

Cited by 6 publications

References 0 publications

ChemInform Abstract: Synthesis of Saturated Cyclic Sulfides

Photochemistry of Thiophen‐2(5H)‐ones

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The Synthesis of Saturated Cyclic Sulphides

Cited by 6 publications

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Photolytisch induzierte Reaktionen von CpCo(CO)2(Cp = C5H5, C5H4Me, C5Me5 und C5Ph5) mit Thiiran zu dinuklearen 1,2-Ethandithiolato-S-S-Komplexen / Photolytically Induced Reactions of CpCo(CO)2 (Cp = C5H5, C5H4Me, C5Me5 and C5Ph5) with Thiirane Yielding Dinuclear 1,2-Ethanedithiolato-S,S Complexes

Photolytisch induzierte Reaktionen von CpCo(CO)2(Cp = C5H5, C5H4Me, C5Me5 und C5Ph5) mit Thiiran zu dinuklearen 1,2-Ethandithiolato-S-S-Komplexen / Photolytically Induced Reactions of CpCo(CO)2 (Cp = C5H5, C5H4Me, C5Me5 and C5Ph5) with Thiirane Yielding Dinuclear 1,2-Ethanedithiolato-S,S Complexes

ChemInform Abstract: Synthesis of Saturated Cyclic Sulfides

Photochemistry of Thiophen‐2(5H)‐ones

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