147397-60-2Relevant articles and documents
The mercury-mediated decarboxylation (Pesci reaction) of naphthoic anhydrides investigated by microwave synthesis
Moseley, Jonathan D.,Gilday, John P.
, p. 4690 - 4697 (2007/10/03)
The mercury-mediated decarboxylation (Pesci reaction) of several substituted naphthoic anhydrides has been investigated by microwave synthesis. A laboratory microwave reactor was found to be ideal for small-scale preparations of this slow reaction, reducing reaction times from typically four days to less than 1 h for the three-step process. The ionic reaction medium rapidly heated to high temperatures under microwave heating and could be efficiently maintained by low microwave power settings. Generation of stoichiometric CO2 was safely contained within the reaction tubes. A simplified reaction procedure has been developed. For substituted naphthoic anhydrides, 1H NMR analysis of the naphthoate ester derivatives indicated no change in the regioisomer ratio compared to previously reported thermal values.
Photochemistry of substituted 1-naphthylmethyl esters of phenylacetic and 3-phenylpropanoic acid: Radical pairs, ion pairs, and marcus electron transfer
DeCosta, Dayal P.,Pincock, James A.
, p. 2180 - 2190 (2007/10/02)
The ring-subtituted 1-naphthylmethyl esters of phenylacetic (3a-k) and 3-phenylpropanoic (5a-c) acid have been photolyzed in methanol solvent. The major products of these reactions are derived from two critical intermediates, the 1-naphthylmethyl radical/acyloxy radical pair and the 1-naphthylmethyl cation/carboxylate anion ion pair. The radical pair results in formation of the in-cage coupled products 8a-k and 10a-c after loss of carbon dioxide from the acyloxy radical. The ion pair leads to the methyl ethers 6a-k and the carboxylic acids 7 and 9. The competition between the radical and ionic pathways is very dependent upon the substituents on the naphthalene ring. Analysis of these substituent effects results in a proposed mechanism of initial homolytic cleavage of the carbon-oxygen bond of the ester from the excited singlet state. This radical pair then partitions between two pathways: decarboxylation of the acyloxy radical and electron transfer converting the radical pair to the ion pair. The rates of electron transfer are shown to fit Marcus theory in both the normal and the inverted region.
