ChemInform Abstract: SILYLIERUNG VON NITROVERBINDUNGEN 2. MITT. TRIMETHYLSILYLIERUNG VON TRINITROMETHAN

Ioffe, Sema L.; Kashutina, M. V.; Shitkin, V. M.; Levin, A. A.; Тартаковский, В. А.

doi:10.1002/chin.197332355

Cited by 4 publications

(2 citation statements)

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“…46,56,58,61,65,[71][72][73]79 In 1972 Ioffe and co-workers80 suggested using the silyl esters of nitronic acids as a 1,3-dipolar component, which unlike their alkyl analogues is stable and retains the ability of cycloaddition to olefins. [81][82][83][84][85][86][87][88][89][90][91][92] The intramolecular reactions of the nitronate group with double bonds are known too. For instance, the interaction of tetranitromethane with one of the double bonds of hexa-1,5-diene gives a nitronic ester which is then added to the other double bond forming bicyclic compound 2 (Scheme l).…”

Section: Synthesismentioning

confidence: 99%

Synthesis, reactions, and properties of oxygen-nitrogen-oxygen systems

Rudchenko¹

1993

Chem. Rev.

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Section: Synthesismentioning

confidence: 99%

Synthesis, reactions, and properties of oxygen-nitrogen-oxygen systems

Rudchenko¹

1993

Chem. Rev.

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“…Isoxazolidine 2-oxide anions (9) were proposed as intermediates from the addition of aryl nitromethanenitronate anions to alkenes,6 and a similar anion (10) was a proposed intermediate from alkaline hydrolysis of a silyl ether (11). 8 Each anion [(9) and (lo)] with sodium, potassium, or other 'hard' counterions thermolysed to give a dihydroisoxazole along with a metal nitrate. None or only trace amounts of the dihydroisoxazole 2-oxide and a metal nitrite were produced; however, this was the preferred product pair when the counterion was silver, a soft ~a t i o n .…”

mentioning

confidence: 99%

Nitrodibromoacetonitrile: an agent for bromination and for the formation of adducts formally derived from cyanonitrocarbene

Boyer¹,

Manimaran²

1989

J. Chem. Soc., Perkin Trans. 1

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The reactions of nitrodibromoacetonitrile (N DBA) with alkenes, aromatic compounds, amines, and sulphides have been studied. Products were formally derived from bromine or nitrocyanocarbene except for bis(2-bromocyclohexyl)nitroacetonitrile (1 3), an adduct (2: 1 ) obtained from cyclohexene and N D BA. 2,3-Dimet hyl but -2-ene was converted into 3-cyano-4,4,5,5tetra met hyl-4,5-di hydroisoxazole 2-oxide (1 5) and 2,3-dibromo-2,3-dimethylbutane (I 6). meso-I ,2-Dibromo-I ,2-diphenylethane was obtained from trans-stilbene. In a reaction catalysed by copper, benzene and NDBA gave benzoyl cyanide. From anthracene, phenol, and cupric acetylacetonate, 9,1O-dibromoanthracene, 4bromophenol, and cupric bromoacetylacetonate were obtained respectively. Dimethyl sulphide, tetrahydrothiophene, and triethylamine afforded the corresponding sulphonium-(30) and (31 ) and ammonium cyanomethylide-(33) t derivatives and, with the latter, co-formation of triethylammonium bromide.Rationales for the reactions are discussed.Abstraction of a 'positive' substituent from bromotrinitromethane,' iodotrinitromethane,2 trinitr~acetonitrile,~ and tetra-nitromethane4 by an alkene lead to the formation of nitronate esters (4) [isolated as isoxazolidine derivatives (6) and polynitro compounds (5)J5 Carbenium nitronates (1'2) t--+ polynitromethanides (1 , 3) have been proposed as intermediates (Scheme 1).Certain metal trinitromethanide salts reacted with cyclohexene in aprotic solvents at 20-50 "C to give 3a,4,5,6,7,7ahexahydro-3-nitro-1,2-benzisoxazole 2-oxide (7),5 Scheme 2. Polynitromethanide salts and alkenes generally gave similar reactions. 5 3 6 The intermediacy of dinitrocarbene (8) was considered; ' however, it was not established that ejection of * We are indebted to Dr.

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