- Trimethylgermylation and trimethylsilylation of N,N-dialkylacetamides and application of their anions to the Peterson-type reaction
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Base-assisted trimethylsilylation and trimethylgermylation of N,N-dimethylacetamide (1a) or 1-acetylpiperidine (1b) were carried out.The germyl group was introduced stepwise onto the methyl carbon of the acetyl group to give mono- (3), bis- (6), or tris(trimethylgermyl)acetamides (9b), respectively, in high yields, whereas under similar conditions the second silyl group was usually introduced at the carbonyl-oxygen.The Peterson-type reaction of N,N-dimethyl(trimethylgermyl)(trimethylsilyl)acetamide (5a) with aldehydes gave preferentially N,N-dimethyl-2-(trimethylgermyl)-2-alkenamides (13).
- Urayama, Shin'ichi,Inoue, Sumie,Sato, Yoshiro
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- α-Silyl Amides: Effective Bifunctional Lynchpins for Type i Anion Relay Chemistry
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Lynchpins comprising α-silyl amides have been validated for type I anion relay chemistry (ARC) to permit ready access to γ-ketoamides. Importantly, the ARC protocol can be run at ambient temperature without the need of additional reagents to trigger the [
- Montgomery, Thomas D.,Smith, Amos B.
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- A facile synthesis of 4(3H)-pyrimidinones via [4 + 2] cycloaddition utilizing trimethylsilylketene
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The [4+2]cycloaddition reaction utilizing trimethylsilylketene with 1,3-diaza-1,3-dienes smoothly proceeded to give the desired cycloadducts, 4(3H)-pyrimidinones, in moderate to high yields.
- Arai, Shigeru,Sakurai, Takuya,Asakura, Hitomi,Fuma, Shin-Ya,Shioiri, Takayuki,Aoyama, Toyohiko
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p. 2283 - 2287
(2007/10/03)
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- Dialkylamino- and alkoxytrialkylstannanes as reagent for synthesis of organoboryl (trialkylsilyl) ketenes
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Dialkylamino- and alkoxytrialkylstannanes have been studied as N- and O-nucleophilic reagents in substitution reactions at the B-Br bond.The previously unknown bis(dialkylamino)- and dialkoxyboryl trialkylsilyl ketenes were synthesized.Some peculiarities of the reactivity of these compounds have been studied. - Key words: dialkylaminotrialkylstannane, alkoxytrialkylstannane, synthesis; borylsilyl ketene, methanolysis, aminolysis.
- Nikolaeva, S. N.,Zolotareva, A. S.,Ponomarev, S. V.,Petrosyan, V. S.
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p. 857 - 861
(2007/10/02)
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- NEW ACCESS TO FUNCTIONALIZED DICHLOROPHOSPHINES: SYNTHESIS OF TWO COORDINATED PHOSPHORUS HETEROCYCLES.
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An easy access to functionalized dichlorophosphines 2, 4, 5, 7 is described, and these compounds are dehydrochlorinated in situ with DABCO and trapped by a diene or a diazocompound to give phosphabenzenes or diazophospholes.
- Pellon, Pascal,Hamelin, Jack
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p. 5611 - 5614
(2007/10/02)
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- REACTIONS OF TRIETHYLGERMYLLITHIUM WITH N,N-DIALKYLATED CARBOXAMIDES
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The reactions of triethylgermyllithium with N,N-dialkylated carboxamides have been investigated.N,N-Dimethylacetamide, N,N-dimethylpivalamide, N,N-diethyltrifluoroacetamide and N,N-diethylbenzamide act on triethylgermyllithium, which is made from bis(triethylgermyl)mercury and lithium in hexane, to release the corresponding acyltriethylgermanes as the principal product.The regioselectivity of the present reactions was found to depend markedly on the reaction conditions and the nature of the acyl fragment of amides.Thus, triethylgermyllithium reacts with N,N-dimethylacetamide as metallating agent to give lithium N,N-dimethylacetamide, if the reaction is carried out in tetrahydrofuran solution.Mechanistic interpretations of these results are discussed.
- Bravo-Zhivotovskii, D. A.,Pigarev, S. D.,Kalikhman, I. D.,Vyazankina, O. A.,Vyazankin, N. S.
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