1478-41-7Relevant articles and documents
Synthesis and reactivity of substituted α-carbonylphosphonites and their derivatives
Prishchenko, Andrey A.,Livantsov, Mikhail V.,Novikova, Olga P.,Livantsova, Ludmila I.,Petrosyan, Valery S.
experimental part, p. 352 - 372 (2012/08/28)
Convenient methods for the synthesis of functionalized organophosphorus compounds containing carbonyl groups as well as di- or trialkoxymethyl fragments attached to phosphorus, and their derivatives, starting from the available derivatives of trivalent phosphorus acids, are proposed, and some properties of the new functionalized organophosphorus compounds are presented. So, the alkylation and acylation reaction of (dialkoxymethyl) phosphonites and their analogs have been studied. It is found that the Arbuzov rearrangement of these compounds was accompanied by the phosphorus-carbon bond cleavage with unique retention of the three-coordinate phosphorus.
CONVENIENT AND OPTIMIZED PROCEDURE FOR THE SYNTHESIS OF DI- AND TRIALKOXYCARBENIUM TETRAFLUOROBORATES
Pindur, U.,Flo, C.
, p. 2307 - 2312 (2007/10/02)
A convenient and optimized procedure for the synthesis of some di- and trialkoxycarbenium tetrafluoroborates under an argon atmosphere and using a specially developed apparatus is described.
Reactions of Electron-Rich Heterocycles with Orthocarboxylic Acid Derivatives, 10. - Formylation and Alkylation of Carbazoles with Ambident Dialkoxycarbenium Tetrafluoroborates
Flo, Camran,Pindur, Ulf
, p. 509 - 514 (2007/10/02)
Carbazole and some derivatives were formylated regioselectively with diethoxycarbenium tetrafluoroborate.The thermodynamically more stable diethoxymethylcarbenium and trimethoxycarbenium ions exhibit ambident electrophilic reactivity as predominant alkylation reagent.
Regioselective, Mild Acylation of 2-Methylindole with Di- and Trialkoxycarbenium Tetrafluoroborates - A Simple Procedure for Deriving 3-Acyl-2-methyl-indoles and 3-Methoxycarbonyl-2-methylindole. Reactions of Electron-rich Heterocycles with Derivatives of Carboxylic Ortho Acids, VII.
Pindur, Ulf,Flo, Camran
, p. 375 - 384 (2007/10/02)
The regioselective acylation of 2-methylindole (2) with acyclic di- and trialkoxycarbenium tetrafluoroborates 1 produces, by way of the stable indolyl-alkoxycarbenium ions 4, the 3-acylated indoles 5a-5c, and the 3-methoxycarbonylindole 5d.The ambident electrophilic cations 1 all react as a1-electrophiles with the very nucleophilic indole 2.In the reaction of 2 with trimethoxycarbenium tetrafluoroborate (2d) methylated products are formed additionally. - Keywords: 3-Acylated 2-methylindoles; Synthesis with di- and trialkoxycarbenium tetrafluoroborates
Benzoisobenzofuran. Formation and Reactions of the Parent and Alkoxy-Substituted Derivatives
Cornejo, Jaime J.,Ghodsi, Shahram,Johnson, R. Douglas,Woodling, Rick,Rickburn, Bruce
, p. 3869 - 3876 (2007/10/02)
Benzoisobenzofuran (1) is formed by base-induced 1,4-elimination of either acetal 9 or 11 and may be isolated in high yield as a cristalline solid.Cycloaddition reactions of preformed 1 have been carried out with various dienophiles.These reactions may also be accomplished by heating the acetals in the presence of dienophiles and acid catalyst, where 1 is generated as an intermediate.The cycloaddition reaction of 1 and maleic anhydride is found to be reversible at higher temperature (slow at 60 deg C).Unsymmetrical dienophiles react with 1 to give equal amounts of regioisomers, and evidence points to lack of regioselectivity under both kinetically controlled and equilibrating conditions.The acetals 9 and 11 are shown to interconvert with acid catalyst at 140 deg C, where 1 is an intermediate of greater stability than the acetals; the equilibrium K for 9 -> ( - ) 11 is approximately unity.Various acid-catalyzed cycloaddition reactions of ortho esters 8 and 10, yielding polysubstituted phenanthrene derivatives, are described.
A Procedure for Diethoxymethylation of Ketones
Mock, William L.,Tsou, Hwei-Ru
, p. 2557 - 2561 (2007/10/02)
Reaction of a number of ketones with diethoxycarbenium fluoroborate in the presence of N,N-diisopropylethylamine at low temperature in methylene chloride results in a preparatively useful conversion to α-(diethoxymethyl) ketones.The method is compatible with arene, nitrile, chloride, and ester functional groups.With unsymmetrically substituted ketones, it is regioselective for the less substituted α-position.In favorable cases α,α'-dialkylation occurs.Conjugated ketones react normally at the saturated position adjacent to the carbonyl group.The mechanism of the reaction is considered.