S(RN)1 reactions of anthraquinone alkylating agents
The C-alkylation reaction of three reductive alkylating agents prepared from 2-methylanthraquinone by 2-nitropropane anion is shown to proceed by the S(RN)1 mechanism. The S(RN)1 mechanism is confirmed by the leaving group effect and the inhibitory effect of dioxygen, p-dinitrobenzene, cupric chloride and di-tert-butylnitroxide. This reaction can be extended to 1-methyl-3-nitropyrolidin-2-one anion.
Crozet,Vanelle,Jentzer,Donini,Maldonado
p. 11253 - 11262
(2007/10/02)
REACTIONS DE SUBSTITUTION SRN1 EN SERIE QUINONIQUE
Salts derived from 2-nitropropane react with 2-(halomethyl)-9,10-anthracenedione or triethylammonium derivative by a SRN1 mechanism.The operation of this mechanism is confirmed by the leaving group effect and by the inhibitory effect of di-tert-butylnitroxide.A base-promoted nitrous acid elimination gives a 9,10-anthracenedione bearing a trisubstituted ethylenic double bound in the 2 position.
Crozet, Michel P.,Jentzer, Olivier,Vanelle, Patrice
p. 5531 - 5534
(2007/10/02)
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