Thermal conversion of the endo-peroxides of the arylfurans (1) in a polar aprotic solvent leads to aroylenol esters (4) and diaroyl epoxides (3), the predominance of one over the other being concentration dependent. The results can be rationalized on the basis of the intermediacy of dipolar species, e.g. (6a) and/or (7a - d), which are formed in the first stages of the reaction and can react intra- and/or inter-molecularly. The behaviour of the peroxides (1) in an apolar solvent suggests that in this case the epoxides (3) are predominantly formed by a different route, probably involving an intramolecular synchronous rearrangement.
Photosensitized oxidation of furans. Part 7. Solvent effects in thermal conversion of the endo-peroxides of arylfurans / Graziano, M. L.; Iesce, M. R.; Chiosi, S.; Scarpati, Rachele. - (1983), pp. 2071-2074. [10.1039/p19830002071]
Photosensitized oxidation of furans. Part 7. Solvent effects in thermal conversion of the endo-peroxides of arylfurans
Graziano M. L.;Iesce M. R.;
1983
Abstract
Thermal conversion of the endo-peroxides of the arylfurans (1) in a polar aprotic solvent leads to aroylenol esters (4) and diaroyl epoxides (3), the predominance of one over the other being concentration dependent. The results can be rationalized on the basis of the intermediacy of dipolar species, e.g. (6a) and/or (7a - d), which are formed in the first stages of the reaction and can react intra- and/or inter-molecularly. The behaviour of the peroxides (1) in an apolar solvent suggests that in this case the epoxides (3) are predominantly formed by a different route, probably involving an intramolecular synchronous rearrangement.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
