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Organosilicon Chemistry
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Organosilicon Chemistry

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (31 August 2011) | Viewed by 31816

Special Issue Editor

Prof. Dr. Scott Sieburth

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Department of Chemistry, Temple University, 1901 N. 13th Street, Philadelphia, PA 19122, USA
Interests: synthetic organic and medicinal chemistry; organosilicon chemistry

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Published Papers (4 papers)

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Research

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243 KiB  
Article
Lipase-Catalyzed Kinetic Resolution of Aryltrimethylsilyl Chiral Alcohols
by Dayvson J. Palmeira, Juliana C. Abreu and Leandro H. Andrade
Molecules 2011, 16(11), 9697-9713; https://doi.org/10.3390/molecules16119697 - 23 Nov 2011
Cited by 8 | Viewed by 6957
Abstract
Lipase-catalyzed kinetic resolution of aryltrimethylsilyl chiral alcohols through a transesterification reaction was studied. The optimal conditions found for the kinetic resolution of m- and p-aryltrimethylsilyl chiral alcohols, led to excellent results, high conversions (c = 50%), high enantiomeric ratios ( [...] Read more.
Lipase-catalyzed kinetic resolution of aryltrimethylsilyl chiral alcohols through a transesterification reaction was studied. The optimal conditions found for the kinetic resolution of m- and p-aryltrimethylsilyl chiral alcohols, led to excellent results, high conversions (c = 50%), high enantiomeric ratios (E > 200) and enantiomeric excesses for the remaining (S)-alcohol and (R)-acetylated product (>99%). However, kinetic resolution of o-aryltrimethylsilyl chiral alcohols did not occur under the same conditions applied to the other isomers. Full article
(This article belongs to the Special Issue Organosilicon Chemistry)
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381 KiB  
Article
Dissociation of the Disilatricyclic Diallylic Dianion [(C4Ph4SiMe)2]−2 to the Silole Anion [MeSiC4Ph4]− by Halide Ion Coordination or Halide Ion Nucleophilic Substitution at the Silicon Atom
by Jang-Hwan Hong
Molecules 2011, 16(10), 8451-8462; https://doi.org/10.3390/molecules16108451 - 10 Oct 2011
Cited by 6 | Viewed by 5617
Abstract
The reductive cleavage of the Si-Si bond in 1,1-bis(1-methyl-2,3,4,5-tetraphenyl-1-silacyclopentadiene) [(C4Ph4SiMe)2] (1) with either Li or Na in THF gives the silole anion [MeSiC4Ph4]− (2). The head-to-tail dimerization of [...] Read more.
The reductive cleavage of the Si-Si bond in 1,1-bis(1-methyl-2,3,4,5-tetraphenyl-1-silacyclopentadiene) [(C4Ph4SiMe)2] (1) with either Li or Na in THF gives the silole anion [MeSiC4Ph4]− (2). The head-to-tail dimerization of the silole anion 2 gives crystals of the disilatricyclic diallylic dianion [(C4Ph4SiMe)2]−2 (3). The derivatization of 3 (crystals) with bromoethane (gas) under reduced pressure provides [(MeSiC4Ph4Et)2] (4) quantitatively. The reverse addition of 3 in THF to trimethylsilyl chloride, hydrogen chloride, and bromoethane in THF gives 1-methyl-1-trimethylsilyl-1-silole [Me3SiMeSiC4Ph4] (6), 1-methyl-2,3,4,5-tetraphenyl-1-silacyclo-3-pentenyl-1-methyl-1-silole [C4Ph4H2SiMe-MeSiC4Ph4] (7), and 1-methyl-2,5-diethyl-2,3,4,5-tetraphenyl-1-silacyclo-3-pentenyl-1-methyl-1-silole [C4Ph4Et2SiMe-MeSiC4Ph4] (8), respectively. The reaction products unambiguously suggest that the silole anion [MeSiC4Ph4]− is generated by coordination of the chloride ion at the silicon atom in 3 or by the nucleophilic substitution of either chloride or bromide ion at one of two silicon atoms in 3. The quenching reaction of 3 dissolved in THF with water gives 1,2,3,4-tetraphenyl-2-butene, the disiloxane of 1-methyl-2,3,4,5-tetraphenyl-1-silacyclo-3-pentenyl [O(MeSiC4Ph4)2] (10) and methyl silicate. Full article
(This article belongs to the Special Issue Organosilicon Chemistry)
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419 KiB  
Communication
Synthesis and NMR-Study of the 2,3,4,5-Tetraethylsilole Dianion [SiC4Et4]2−•2[Li]+
by Jang-Hwan Hong
Molecules 2011, 16(9), 8033-8040; https://doi.org/10.3390/molecules16098033 - 16 Sep 2011
Cited by 12 | Viewed by 5240
Abstract
The previously unknown silole dianion [SiC4Et4]2−•2[Li]+ (3) was prepared by the sonication of 1,1-dichloro-2,3,4,5-tetraethyl-1-silacyclopentadiene [Cl2SiC4Et4, 2] with more than four equivalent of lithium in THF. 1H-, [...] Read more.
The previously unknown silole dianion [SiC4Et4]2−•2[Li]+ (3) was prepared by the sonication of 1,1-dichloro-2,3,4,5-tetraethyl-1-silacyclopentadiene [Cl2SiC4Et4, 2] with more than four equivalent of lithium in THF. 1H-, 13C-, and 29Si-NMR data of 3 are compared with those of the reported silole dianion [SiC4Ph4]2−. Trapping of 3 with trimethylchlorosilane gave 1,1-bis(trimethylsilyl)-2,3,4,5-tetraethyl-1-silacyclopentadiene [(Me3Si)2SiC4Et4, 4] in high yield. The silole of 2 was synthesized in high yield in three steps by a modified procedure using Cp2ZrCl2 via Cp2ZrC4Et4 and 1,4-dibromo-1,2,3,4-tetraethyl-1,3-butadiene. Full article
(This article belongs to the Special Issue Organosilicon Chemistry)
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Review

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582 KiB  
Review
Recent Applications of the (TMS)3SiH Radical-Based Reagent
by Chryssostomos Chatgilialoglu and Jacques Lalevée
Molecules 2012, 17(1), 527-555; https://doi.org/10.3390/molecules17010527 - 6 Jan 2012
Cited by 88 | Viewed by 13440
Abstract
This review article focuses on the recent applications of tris(trimethylsilyl)silane as a radical-based reagent in organic chemistry. Numerous examples of the successful use of (TMS)3SiH in radical reductions, hydrosilylation and consecutive radical reactions are given. The use of (TMS)3SiH [...] Read more.
This review article focuses on the recent applications of tris(trimethylsilyl)silane as a radical-based reagent in organic chemistry. Numerous examples of the successful use of (TMS)3SiH in radical reductions, hydrosilylation and consecutive radical reactions are given. The use of (TMS)3SiH allows reactions to be carried out under mild conditions with excellent yields of products and remarkable chemo-, regio-, and stereoselectivity. The strategic role of (TMS)3SiH in polymerization is underlined with emphasis on the photo-induced radical polymerization of olefins and photo-promoted cationic polymerization of epoxides. Full article
(This article belongs to the Special Issue Organosilicon Chemistry)
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