99682-65-2Relevant academic research and scientific papers
The Chemistry of Phthalide-3-carboxylic Acid. II. Decarboxylation of Salts in the Presence of Aldehydes
Dibbens, Justin A.,Prager, Rolf H.,Schiesser, Carl H.,Wells, Andrew J.
, p. 913 - 920 (2007/10/02)
Salts of phthalide-3-carboxylic acid decarboxylate in the presence of aromatic aldehydes to give mixtures of the 3-(arylhydroxymethyl)phthalide (2) and the 2-aryl-3-hydroxyindenone (3).The former may be obtained exclusively in the presence of the weak proton donor, triethyl(2-phenylethyl)ammonium chloride, and the latter in the presence of crown ethers or after longer reaction times.A study of the effect of different cations allows a mechanism to be deduced.
THE CHEMISTRY OF PHTALIDE-3-CARBOXYLIC ACID - I DECARBOXYLATION ON THE PRESENCE OF THE ALDEHYDES
Prager, Rolf H.,Schiesser, Carl H.
, p. 1517 - 1522 (2007/10/02)
The decarboxylation of phthalide-3-carboxylic acid (3-oxo-1,3-dihydroisobenzofuran-1-carboxylic acid) has been studied in the melt, in dimethylsulfoxide, and in the presence of aromatic aldehydes.The latter are efficiently trapped to produce mixtures of 3-arylidene-phthalides and 3-(arylhydroxymethyl)phthalides.Kinetic and other evidence supports the proposal that this reaction occurs in a tight cyclic transition state.
