Organosilicon and Tin Alkylthiols

Stamm, W

doi:10.1021/jo01046a540

Cited by 19 publications

(7 citation statements)

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“…6b gefunden und zweimal eine geringe Menge des symmetrischen Tetraphenylethans 5. Auch cis-N-Benzoyl-2-benzyl-3-phenylaziridin (2b) verhielt sich ganz analog (Versuch 3, wiihrend N-Benzoyl-2,2-dimethylaziridin (8) ausschliefllich das erwartete Oxazolin 9 liefene (Versuch 6). Friiher schon4) war aus N-Benzoyl-2-phenylaziridin genauso nur das entspr.…”

unclassified

Friedel‐Crafts‐Reaktion einiger N‐Acylaziridine: Oxazoline als Zwischenstufen

Mall

Buchholz

Stamm

1994

Archiv der Pharmazie

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Without heat supply, AIC13 and 3-substituted 1-acyl-2-phenylaziridines la,b, and 2b in benzene provided the respective Friedel-Crufts products 3a,b, and 4b (acylated 1 -substituted 2,2-diphenylethylamines) which in part were further converted to 1,1,2.2-tetraphenylethane (5). Oxazolines 6a,b, and 7b were also found. It is shown by means of 2,4,5-triphenyloxazoline 6b that oxazolines are intermediates for 3.4, and 5. The uncommon heterolysis of these particular oxazolines is discussed.

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unclassified

Friedel‐Crafts‐Reaktion einiger N‐Acylaziridine: Oxazoline als Zwischenstufen

Mall

Buchholz

Stamm

1994

Archiv der Pharmazie

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“…13 2-(Trimethylsilyl)ethanethiol and 2-(trimethylsilyl)ethyl sulfides can be also prepared by photochemical addition of hydrogen sulfide to vinyltrimethylsilane (Scheme 2). 20 2-(Trimethylsilyl)ethyl sulfides have been prepared in good yields by reaction of 2-(trimethylsilyl)ethanethiol with halogeno derivatives in the presence of a base (Scheme 2) 11 or from epoxides or a strained ring. 21,22 From this reagent, unsaturated sulfides have also been synthesised as intermediates in the synthesis of natural products and composite materials (see part 2.2.1).…”

Section: Synthesis Of 2-(trimethylsilyl)ethanethiol and Derivativesmentioning

confidence: 99%

The 2-(Trimethylsilyl)ethyl Sulfur Group in Synthesis

Chambert¹,

Désiré²,

Décout³

2002

Synthesis

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The trimethylsilylethyl sulfur group present in 2-(trimethylsilyl)ethyl sulfides, sulfones, sulfoxides and in 2-(trimethylsilyl)ethylsulfonamido derivatives has proved its potential in synthesis. Presence of sulfur and silicon on adjacent carbon atoms provides routes for preparing interesting sulfur or non-sulfur, silicon or non-silicon derivatives like thiols, methyl disulfides, thioesters, thiocyanates, unsaturated derivatives and amines through the selective removal of the trimethylsilylethyl or the trimethylsilyl group. 5 Conclusion

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“…Sulfur functionality was introduced by the photochemical addition of thiolacetic acid to trimethylvinylsilane (1) to yield 2-(trimethylsilyl)ethyl thioacetate (3) and to trimethylallylsilane (2) to yield 3-(trimethylsilyl)propyl thioacetate (4).1,3,10 Hydrolysis of 3 with aqueous base yields 2-(trimethylsilyl)ethanethiol (5). 6 The thiol was chloromethylated by treatment with HC1 and paraformaldehyde to yield 2-(trimethylsilyl)ethyl chloromethyl sulfide (7).20,21 Reduction of the chloromethyl sulfide with L1AIH4 in THF yields 9. Oxidation of 9 with m-chloroperbenzoic acid yields the corresponding sulfone 11.…”

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confidence: 99%