78631-75-1Relevant academic research and scientific papers
Meta, para and ortho double exo nucleophilic additions of trimethylsilylester enolates derived from saturated and unsaturated carboxylic acids to tricarbonylchromium complexes of aryl ethers: dearomatizing cyclization to lactones
Rudler, Henri,Comte, Virginie,Garrier, Eva,Bellassoued, Moncef,Chelain, Evelyne,Vaissermann, Jaqueline
, p. 284 - 298 (2001)
Potassium enolates derived from saturated and unsaturated bis(trimethylsilyl) ketene acetals react with tricarbonylchromium complexes of anisole and diphenylether to give, in addition to α-arylcarboxylic acids, the mono addutcts, lactones, arising from a double exo nucleophilic addition. The latter were not observed in the case of benzenetricarbonylchromium. The intermediate dienol ethers could be isolated and fully characterized by X-ray crystallography. The influenece of the nature of the substituents on the ketene acetals, of the nature of the oxidant, and of the nature of the ester enolates on the course of the reaction has been established and will be discussed.
Unexpected formation of 3,3a,4,7a-tetrahydrobenzofuran-2,5-dione as well as arene carboxylic acids upon formal double exo nucleophilic addition of R1R2C-COO- to anisolechromium tricarbonyl complexes
Bellassoued, Moncef,Chelain, Evelyne,Collot, Jerome,Rudler, Henri,Vaissermann, Jacqueline
, p. 187 - 188 (2007/10/03)
Bis(trimethylsily)ketene acetals of the general structure 2 (R1 = H,Me,R2 = Me,Et,Pr(i),CMe = CH2) react at -78°C in the presence of Bu(t)OK with a series of arenechromium tricarbonyl complexes 3 to give as expected, after oxidation with I2 followed by silica gel chromatography, arylcarboxylic acids 7. In the case of anisolechromium tricarbonyl 8, besides the m-methoxyarylcarboxylic acids, tetrahydrobenzofuran-2,5-diones 11, are formed as the result of a double nucleophilic addition.
2-Methyl-1-phenyl-1-propenyllithium. A Vinyllithium Derivative Showing Catalyzed Transmetalation
Knorr, Rudolf,Lattke, Ernst
, p. 2116 - 2131 (2007/10/02)
Full preparative and kinetic details are given for the apparent vinyl-to-allyl anion rearrangement of the title compound 1.The rapid and quantitative formation of the allyllithium derivative 7 is shown to be catalyzed by 2-methyl-1-phenyl-1-propene (2).An intermolecular transmetalation mechanism with de-aggregation and ionization steps is suggested to explain the orders of reaction, parameters of activation, and solvent dependency.
