30012-51-2Relevant articles and documents
Photochemical Rearrangement of α-Chloro-Propiophenones to α-Arylpropanoic Acids: Studies on Chirality Transfer and Synthesis of (S)-(+)-Ibuprofen and (S)-(+)-Ketoprofen
Sonawane, Harikisan,Bellur, Nanjundiah S.,Kulkarni, Dilip G.,Ayyangar, Nagaraj R.
, p. 1243 - 1260 (2007/10/02)
A new single-step efficient photochemical approach for α-arylpropanoic acids (4) from α-chloro-propiophenones (5) is described.It involves carbonyl triplet excited state directed 1,2-aryl migration of the aryl group which has been found to be highly dependent upon the nature of the aryl substituent.The mode of the rearrangement is probed by the study of the photobehaviour of a set of optically active α-chloro-propiophenones.The results suggest that the nature of the carbonyl triplets (n, ?*/ ?, ?*) plays an important role in the chirality transfer.This method finds application in the synthesis of optically active ibuprofen (4e) and ketoprofen (26), though in moderate optical yields.
Oxidative decarboxylation of naproxen
Bosca,Martinez-Manez,Miranda,Primo,Soto,Vano
, p. 479 - 482 (2007/10/02)
The decarboxylation of naproxen (1H) and its salt (1-) was achieved by means of chemical [Ce(IV) or S2O8/2-] and electrochemical oxidation. The product patterns were compatible with mechanisms involving single-electron transfer from the pl-system or the carboxylate moiety. The results are discussed in connection with the involvement of electron-transfer processes in the reported phototoxicity of naproxen.