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Paramagnetic Species in the Spontaneous and Photoinduced Reaction of Nitrocompounds With BU4Nbh4

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Several nitroalkanes and nitroarenes have been reacted with BH4NBu4 either in THF or in benzene. Nitroalkanes do not give any spontaneous reaction, but upon photolysis afford the hitherto undetected boroxy nitroxides, RN(O.)OBlH3, in benzene and the tetrahydrofuranyloxy nitroxides in THF. 1,4-Dinitrobenzene reacted spontaneously with the borohydride either in THF or in benzene to give the corresponding radical anion via a single electron transfer (SET) process; nitrobenzene reacted spontaneously only in THF, while in benzene the formation of the radical anion only occurred upon photolysis. 1,8-Dinitro- and 1,9,5-trinitrobenzene, despite their small E1/2 values, do not give electron 2 transfer, but undergo addition by a hydride anion to give Meisenheimer complexes; on the other hand, 2,4,6-tri-tert-butyl nitrobenzene, which has a reduction potential more negative than the other nitroarenes, behaves more like nitroalkanes.

Affiliations: 1: I.Co.C.E.A.-C.N.R., Via della Chimica 8 1-40064 Ozzano Emilia, Italy; 2: Dipartimento di Chimica Organica A. Mangini Università di Bologna Via S. Donato 15, 1-40127 Bologna, Italy


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