Showing papers by "Marcello Tiecco published in 1990"
TL;DR: In this paper, it was shown that the oxidation of diphenyl diselenide with ammonium peroxydisulfate represents a very simple method of generating phenylselenium cations in the absence of nucleophile counterions.
Abstract: The results described in the present paper indicate that the oxidation of diphenyl diselenide with ammonium peroxydisulfate represents a very simple method of generating phenylselenium cations in the absence of nucleophile counterions
83 citations
TL;DR: The reaction of methyl ketones with catalytic amounts of diphenyl diselenide and an excess of ammonium peroxydisulfate in methanol proceeds smoothly to afford α-keto acetals in good yield and the phenylselenenylating agent is regenerated.
Abstract: The reaction of methyl ketones with catalytic amounts of diphenyl diselenide and an excess of ammonium peroxydisulfate in methanol proceeds smoothly to afford α-keto acetals in good yield. In some cases reaction yields were increased by using stoichiometric amounts of PhSeSePh. It is suggested that the oxidation of PhSeSePh by (NH 4 ) 2 S 2 O 8 produces a very electrophilic phenylselenenylating agent that effects the methoxyselenenylation of the methyl ketones. The addition products so formed react with (NH 4 ) 2 S 2 O 8 to afford the methoxydeselenenylation products; the phenylselenenylating agent is thus regenerated. Thus, the entire process can be effected in one pot and with catalytic amounts of PhSeSePh
53 citations
TL;DR: In this paper, 4-Pentenenenitriles reacted with PhI(OAc)2 in acetic acid in the presence of 48% HBF4 at 70 ° C to afford the dihydro-5-acetoxymethyl-2(3H)-furanones in good yields.
27 citations
TL;DR: The reaction of substituted 4-pentenonitriles with 50% sulphuric acid at 100 °c afforded γ-lactones in moderate to good yield.
Abstract: The reaction of substituted 4-pentenonitriles with 50% sulphuric acid at 100 °c afforded γ-lactones in moderate to good yield.