2-Alkyl-2-phenyl-3,3-dimethylindolines, obtained by 1,2 organolithium addition to 2-phenyl-3,3-dimethyl-3H-indole, are converted into a new series of aminoxyls by oxidation with m-chloroperoxybenzoic acid. Attempts to synthesise, in a similar way, suitable precursors such as 1,2-dihydro-2-phenyl-2-alkylbenzothiazole, 1,2-dihydro-2-phenyl-2-alkylbenzoxazole and 1,2-dihydro-2-phenyl-2-alkyl-4H-3,1-benzoxazin-4-one for other new aminoxyls failed. In fact, 2-phenylbenzothiazole, 2-phenylbenzoxazole and 2-phenyl-4H-3,1-benzoxazin-4-one react with organolithium reagents affording products deriving from ring opening. Crystal structures of 2,3-dimethyl-3-phenyl-3H-indole and bis(2-triphenylmethylaminophenyl) disulfide are also described.

Synthesis of a new series of indolinic aminoxyls. Reaction of indoles, 2-phenylbenzothiazole, 2-phenylbenzoaxozole and 2-phenyl-1,2-dihydro-4H-3,1-benzoxazin-4-one with organolithium reagents / Tommasi, Giampaolo; Bruni, Paolo; Greci, Lucedio; Sgarabotto, Paolo; Righi, Lara; Petrucci, Rita. - In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS II. - ISSN 0300-9580. - STAMPA. - 10:(1999), pp. 2123-2128. [10.1039/a904092g]

Synthesis of a new series of indolinic aminoxyls. Reaction of indoles, 2-phenylbenzothiazole, 2-phenylbenzoaxozole and 2-phenyl-1,2-dihydro-4H-3,1-benzoxazin-4-one with organolithium reagents.

Rita PETRUCCI
1999

Abstract

2-Alkyl-2-phenyl-3,3-dimethylindolines, obtained by 1,2 organolithium addition to 2-phenyl-3,3-dimethyl-3H-indole, are converted into a new series of aminoxyls by oxidation with m-chloroperoxybenzoic acid. Attempts to synthesise, in a similar way, suitable precursors such as 1,2-dihydro-2-phenyl-2-alkylbenzothiazole, 1,2-dihydro-2-phenyl-2-alkylbenzoxazole and 1,2-dihydro-2-phenyl-2-alkyl-4H-3,1-benzoxazin-4-one for other new aminoxyls failed. In fact, 2-phenylbenzothiazole, 2-phenylbenzoxazole and 2-phenyl-4H-3,1-benzoxazin-4-one react with organolithium reagents affording products deriving from ring opening. Crystal structures of 2,3-dimethyl-3-phenyl-3H-indole and bis(2-triphenylmethylaminophenyl) disulfide are also described.
1999
01 Pubblicazione su rivista::01a Articolo in rivista
Synthesis of a new series of indolinic aminoxyls. Reaction of indoles, 2-phenylbenzothiazole, 2-phenylbenzoaxozole and 2-phenyl-1,2-dihydro-4H-3,1-benzoxazin-4-one with organolithium reagents / Tommasi, Giampaolo; Bruni, Paolo; Greci, Lucedio; Sgarabotto, Paolo; Righi, Lara; Petrucci, Rita. - In: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS II. - ISSN 0300-9580. - STAMPA. - 10:(1999), pp. 2123-2128. [10.1039/a904092g]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/44143
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