(Thioacetoxy-S-methyl)diorganylsilane und (Mercaptomethyl)diorganylsilane: Synthese und Eigenschaften

Tacke, Reinhold; Becker, B.; Lange, H.

doi:10.1016/0022-328x(90)85346-z

Cited by 7 publications

(2 citation statements)

References 9 publications

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“…Therefore, we used an alternative approach, in which thioacetate 5 was treated with lithium aluminum hydride in ether/pentane on cooling. [7] This allowed us to avoid polymerization and to prepare thiol 9 in good yield (74%).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 4,4-diphenyl-3,4-dihydro-2H-1,4-thiasiline

Suslova

Shainyan

2014

Journal of Sulfur Chemistry

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4,4-Diphenyl-3,4-dihydro-2H-1,4-thiasiline (3) was synthesized starting from diphenyl(divinyl)silane by a sequence of reactions including free-radical thiylation with thioacetic acid, reduction of thioacetate to thiol, heterocyclization of the latter, oxidation and the Pummerer rearrangement of the cyclic sulfoxide to the unsaturated cyclic organosilicon sulfide. Although compound 3 is hydrolytically more stable than its Si-dimethylated analogue, both compounds are hydrolyzed to the corresponding siloxanes with the cleavage of the Si−C sp2 rather than the Si−C sp3 bond. A theoretical rationalization for this is given. hv, D

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Section: Resultsmentioning

confidence: 99%

Synthesis of 4,4-diphenyl-3,4-dihydro-2H-1,4-thiasiline

Suslova

Shainyan

2014

Journal of Sulfur Chemistry

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“…To successfully apply our novel asymmetric catalytic hydrosilylation, it was critical to develop an efficient synthesis of dehydroalanine ester 8a/b . N -Alkylation of dehydroalanine 9 , with silane 10 proved challenging, as both the anion of 9 and silane 10 were shown to be unstable under the reaction conditions, and the union of these two fragments did not proceed sufficiently rapidly to overcome these inherent instabilities. After extensive evaluation, NaHMDS and DMF were found to be the optimal combination of base and solvent.…”

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confidence: 99%

Asymmetric Synthesis of N-Boc-(R)-Silaproline via Rh-Catalyzed Intramolecular Hydrosilylation of Dehydroalanine and Continuous Flow N-Alkylation

et al. 2016

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An asymmetric synthesis of a silicon-containing proline surrogate, N-Boc-(R)-silaproline (1), is described. Starting from N-Boc-dehydroalanine ester, deprotonation, followed by N-alkylation with chloromethyldimethylsilane under flow conditions, afforded the N-alkylated product 8 in 91% yield. An unprecedented enantioselective (NBD)2RhBF4/Josiphos 404-1 catalyzed 5-endo-trig hydrosilylation afforded the silaproline ester in 85-90% yield and >95% ee. Subsequent saponification and salt formation upgraded 1 to >99% ee.

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ChemInform Abstract: (Thioacetoxy‐S‐methyl)diorganylsilanes and (Mercaptomethyl)diorganylsilanes: Synthesis and Properties.

1990

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(Thioacetoxy-S-methyl)diorganylsilane und (Mercaptomethyl)diorganylsilane: Synthese und Eigenschaften

Abstract: The novel synthesis of the (thioacetoxy-S-methyl)diorganylsilanes (CH 3 ) 2

Cited by 7 publications

References 9 publications

Synthesis of 4,4-diphenyl-3,4-dihydro-2H-1,4-thiasiline

Synthesis of 4,4-diphenyl-3,4-dihydro-2H-1,4-thiasiline

Asymmetric Synthesis of N-Boc-(R)-Silaproline via Rh-Catalyzed Intramolecular Hydrosilylation of Dehydroalanine and Continuous Flow N-Alkylation

ChemInform Abstract: (Thioacetoxy‐S‐methyl)diorganylsilanes and (Mercaptomethyl)diorganylsilanes: Synthesis and Properties.

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