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1ChemInform Abstract: THE PREPARATION AND REACTIONS OF AN OPTICALLY‐ACTIVE SILYL‐MERCURIAL

C. EABORN,R. A. JACKSON,D. J. TUNE,D. R. M. WALTON

Chemischer InformationsdienstVolume 5, Issue 13 Organoelement Compounds ChemInform Abstract: THE PREPARATION AND REACTIONS OF AN OPTICALLY-ACTIVE SILYL-MERCURIAL C. EABORN, C. EABORNSearch for more papers by this authorR. A. JACKSON, R. A. JACKSONSearch for more papers by this authorD. J. TUNE, D. J. TUNESearch for more papers by this authorD. R. M. WALTON, D. R. M. WALTONSearch for more papers by this author C. EABORN, C. EABORNSearch for more papers by this authorR. A. JACKSON, R. A. JACKSONSearch for more papers by this authorD. J. TUNE, D. J. TUNESearch for more papers by this authorD. R. M. WALTON, D. R. M. WALTONSearch for more papers by this author First published: April 2, 1974 https://doi.org/10.1002/chin.197413347AboutPDF 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 onEmailFacebookTwitterLinkedInRedditWechat No abstract is available for this article. References C. EABORN, R. A. JACKSON, D. J. TUNE, D. R. M. WALTON, THE PREPARATION AND REACTIONS OF AN OPTICALLY-ACTIVE SILYL-MERCURIAL, J. Organomet. Chem., 1973, 63, 85. DOI: 10.1016/S0022-328X(73)80021-X; 10.1016/S0022-328X(73)80021-X CASWeb of Science®Google Scholar Volume5, Issue13April 2, 1974 ReferencesRelatedInformation

1974Chemischer Informationsdienst

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2ChemInform Abstract: THE ABSOLUTE CONFIGURATION OF THE OPTICALLY‐ACTIVE SILYL‐PLATINUM COMPLEX (+)‐TRANS‐(PTCL SI(CH3)(1‐C10H7)C6H5 (P(CH3)2C6H5)2)

C. EABORN,P. B. HITCHCOCK,D. J. TUNE,D. R. M. WALTON

AbstractDer optisch aktive Platin‐Komplex (III) wird durch Behandlung des Silans (I) mit dem cis‐Platin‐Komplex (II) erhalten.

1973Chemischer Informationsdienst

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3The Absolute Configuration of the Optically-Active Silylplatinum Complex (+)-Trans-[ptcl{sime(1-c10h7)ph}(pme2ph)2],

C. Eaborn, P.B. Hitchcock,D.J. Tune, D.R.M. Walton

1973Journal of Organometallic Chemistry（1973）

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4The Absolute Configuration of the Optically-Active Silylplatinum Complex (+)-Trans-[ptcl{sime(1-c10h7)ph}(pme2ph)2],

C. Eaborn,P.B. Hitchcock,D.J. Tune,D.R.M. Walton

Crystallographic data are presented which reveal that the complex (+)-[PtCl {SiMe(1-C10H7)Ph}(PMe2Ph)2] has the absolute configuration (S) which corresponds with that of the (R) (+)-Me(1-C10H7)PhSiH from which it is made.

1973Journal of Organometallic Chemistry（1973）

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5Stereochemistry of the Formation and Cleavage of Silicon–platinum Bonds

C EABORN,DJ TUNE,DRM WALTON

The complex (+)-trans-[PtCl(*SiR3)(PMe2Ph)2], [α]D25+ 72°(I), is formed with a high degree of retention of configuration at silicon from (+)-R3Si*H [R3Si*= Me(1-C10H7)PhSi] and cis-[PtCl2(PMe2Ph)2] in the presence of triethylamine. The (+)-R3Si*H is regenerated with 93% overall retention of configuration when (I) is treated with lithium aluminium hydride, and with rather smaller degrees of retention when (I) is treated with benzenethiol or triethylsilane. Bromine liberates (–)-R3Si*Cl with much racemisation, while iodine gives the racemic chloride. Complex (I) is converted into (+)-trans-[PtBr(*SiR3)(PMe2Ph)2], [α]D25+ 70·0°, and (+)-trans-[Ptl(*SiR3)(PMe2Ph)2], [α]D25+ 54·6°, on treatment with lithium bromide or sodium iodide in acetone.The complex (–)-cis-[PtH(*SiR3)(PPh3)2], [α]D25– 18·5°(II), is formed from (+)-R3Si*H and [Pt(PPh3)2C2H4], with little loss of optical activity, and probably with retention of configuration at silicon; the (+)-R3Si*H is regenerated with 97% overall retention on treatment with lithium aluminium hydride, and with a slightly smaller degree of overall retention on treatment with phenylacetylene, benzenethiol, or benzoyl chloride. It is suggested that the cleavages of the Si–Pt bonds in (I) and (II), and especially those involving reaction or formation of R3Si*H, may occur via oxidative-addition–reductive-elimination sequences, with complete or almost complete retention of configuration at silicon, with the observed losses of activity arising from secondary racemisation; it was shown that (+)-R3Si*H and (more readily)(–)-R3Si*Cl do undergo racemisation in the presence of platinum complexes.Triphenylsilane and cis-[PtCl2(PMe2Ph)2] have been found to react to give trans-[PtH(Cl)(PMe2Ph)2], which then reacts with additional triphenylsilane to give trans-[PtCl(SiPh3)(PMe2Ph)2].(+)-Et(1-C10H7)PhGeH (denoted R′3Ge*H), [α]D25+ 15·0°, reacts with trans-[PtH(Cl)(PMe2Ph)2] to give a complex believed to be (+)-trans-[PtCl*(GeR′3)(PMe2Ph)2], [α]D25+12·9°, and with [Pt(PPh3)2C2H4] to give a complex believed to be (–)-cis-[PtH(*GeR3′)(PPh3)2], [α]D25–6·0°, neither optically pure. Both products are thought to be formed with predominant retention of configuration at germanium.

1973Journal of the Chemical Society Dalton transactions（1973）引用：48

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6The Preparation and Reactions of an Optically-Active Silyl-Mercurial

C EABORN,RA JACKSON,DJ TUNE,DRM WALTON

(−)-Bis[methyl(1-naphthyl)phenylsilyl]mercury, (−)-(R3Si*)2Hg, [α]D25 −19.2°, has been obtained in high yield, but optically impure, from interaction of di-tert-butylmercury and (+)-R3Si*H; the specific rotation, [α]D, of the optically-pure compound is estimated to be > 200°. Cleavage with lithium aluminium hydride gives (+)-R3Si*H, [α]D25 +2.8°, and cleavage with 1,2-dibromoethane followed by reduction of the initially produced (+)-R3Si*Br gives (−)-R3Si*H, [α]D25 −2.4°. UV photolysis of the mercurial gives the disilane (−)-(R3Si*)2, [α]D25 −5.2°; the value of [α]D25 for the optically pure disilane is thought to be > −70°. It is suggested that the configuration is predominantly retained at silicon in the formation and all three cleavages of the (−)-(R3Si*)2Hg.

1973Journal of Organometallic Chemistry（1973）引用：23

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7ChemInform Abstract: STEREOCHEMIE DER SPALTUNG VON SILICIUM‐PLATIN‐BINDUNGEN IN OPTISCH AKTIVEN SILICIUM‐PLATIN‐VERBINDUNGEN

C. EABORN,D. J. TUNE,D. R. M. WALTON

AbstractDie Umsetzung des Silicium‐Platin‐Komplexes (I) mit Lithiumaluminiumhydrid liefert das Silan (II), wobei die Konfiguration am Silicium zu 93% erhalten bleibt.

1973Chemischer Informationsdienst（1973）

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8Stereochemistry of Cleavage of Silicon–platinum Bonds in Optically Active Silicon–platinum Compounds

C EABORN,DJ TUNE,DRM WALTON

The cleavage of the Si–Pt bond in trans-(+)-[PtCl(*SiR3)(PPhMe2)2][R3Si*= MePh(1-naphthyl)Si] by LiAlH4, PhSH, or Et3SiH, and of that in (–)-[PtH(*SiR3)(PPh3)2] by LiAlH4, PhCOCl, PhCCH, or PhSH occurs with predominant retention of configuration at silicon.

1972JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS（1972）引用：24

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9The preparation of optically active germyl- and silylplatinum complexes

C. Eaborn,P.N. Kapoor,D.J. Tune,C.L. Turpin,D.R.M. Walton

The compounds (+)-trans-{PtCl[SiMe(1-C10H7)Ph](PMe2Ph)2}, [α]25D +68.8° (benzene), and (+)-trans-{PtCl[GeEt(1-C10H7)Ph](PMe2Ph)2}, [α]25D +12.9 (benzene), have been prepared from the hydrides (+)-Me(1-C10H7)PhSiH and (+)-Et(1-C10H7)PhGeH. There appears to be little loss of optical activity during the formation of the silicon-platinum compound, but possibly a substantial loss occurs during the formation of the germanium—platinum compound.

1972Journal of Organometallic Chemistry（1972）引用：37

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10ChemInform Abstract: DARST. OPTISCH AKTIVER GERMYL‐ UND SILYL‐PLATIN‐KOMPLEXE

C. EABORN,P. N. KAPOOR,D. J. TUNE,C. L. TURPIN,D. R. M. WALTON

Chemischer InformationsdienstVolume 3, Issue 16 Preparative Organic Chemistry ChemInform Abstract: DARST. OPTISCH AKTIVER GERMYL- UND SILYL-PLATIN-KOMPLEXE C. EABORN, C. EABORNSearch for more papers by this authorP. N. KAPOOR, P. N. KAPOORSearch for more papers by this authorD. J. TUNE, D. J. TUNESearch for more papers by this authorC. L. TURPIN, C. L. TURPINSearch for more papers by this authorD. R. M. WALTON, D. R. M. WALTONSearch for more papers by this author C. EABORN, C. EABORNSearch for more papers by this authorP. N. KAPOOR, P. N. KAPOORSearch for more papers by this authorD. J. TUNE, D. J. TUNESearch for more papers by this authorC. L. TURPIN, C. L. TURPINSearch for more papers by this authorD. R. M. WALTON, D. R. M. WALTONSearch for more papers by this author First published: April 18, 1972 https://doi.org/10.1002/chin.197216434Read 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 onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume3, Issue16April 18, 1972 RelatedInformation

1972Chemischer Informationsdienst

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