Abstract
Comparative study of chemical and light induced ele ctron-transfer reactions of some (anthracen- 9-yl)methanamines is reported. Ceric ammonium nitrate was used to initiate chemically-induced electron-transfer reactions of anthracenemethanamin es. Nitration at the 2-position followed by oxidation was the major pathway observed in the rea ction with CAN while electron-transfer mediated C-N bond cleavage followed by dimerization was the major pathway in photochemical reactions.
Highlights
Ceric ammonium nitrate (CAN) is widely employed in organic synthesis
Results and Discussion (Anthracen-9-yl)methanamines 1a-k having diverse steric and electronic environments around the nitrogen atom were accessed through Leukart reactions between 9-anthraldehyde and appropriate secondary amines (Chart 1).[15,35]
Photoinduced electron-transfer reactions ofmethanamines In continuation, we examined the photochemical transformations of anthracenemethanamines 1a-k
Summary
Ceric ammonium nitrate (CAN) is widely employed in organic synthesis. Most of its applications are based on its potential to act as either a single- or two-electron acceptor and low affinity towards oxygen. Both nitration and oxidation products are formed in the reaction between anthracenes and CAN. Anthracenemethanamines having both amine and arene components are appropriate substrates to examine intramolecular excited state electron-transfer reactions.
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