Tetrahedron letters

S RN 1 reactions of a tetrasubstituted-1, 4-benzoquinone

…, L Giraud, JF Sabuco, P Vanelle, M Barreau

Index: Crozet; Giraud; Sabuco; Vanelle; Barreau Tetrahedron Letters, 1991 , vol. 32, # 33 p. 4125 - 4128

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Citation Number: 35

Abstract

Abstract The C-alkylation reaction of 2-chloromethyl-3, 5, 6-trimethyl-1, 4-benzoquinone by 2- nitropropane anion is shown to proceed by the S RN 1 mechanism. This mechanism is confirmed by the inhibitory effects of dioxygen, p-dinitrobenzene, cupric chloride and di-tert- butylnitroxide. The dioxygen-induced formation of nitro and nitrite derivatives is found for the first time.