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note
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Alternatively, the initially formed DIPEA radical cation A could release a hydrogen radical and/or eject a proton toward the isopropyl substituent, instead of toward the ethyl group. However, such a contribution would not lead to the formation of an ethyl substituted nitrone product, but could provide the proton arsenal for the subsequent nitroalkane reduction process.
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48
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note
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(a) Hydroxyamine 5a was isolated as described in Table 1, entry 7. (b) In a separate reaction, photocatalysis of (2-nitroethyl)benzene, a primary nitroalkane, under condition A′ gives a 58% yield of the corresponding oxime. Presumably, prior to further processing into hydroxylamine, primary dihydroxyamine tends to undergo dehydration to give the oxime product; see ref 12b.
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