Herein, we describe diverse reactivity of (anthracen‐9‐yl)methanamines with a few electron‐deficient acetylenes. Depending on the solvent and concentration, (anthracen‐9‐yl)methanamines reacted with acetylenes through one electron transfer, two electron transfer, or Diels–Alder pathways; and under certain conditions, we observed multiple reaction pathways. We have proposed plausible mechanisms to account for various reactions observed by us. Copyright © 2014 John Wiley & Sons, Ltd.

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Solvent‐dependent diverse reactivity of (anthracen‐9‐yl)methyl sulfides with a few electron‐deficient acetylenes is described. Diversity in reactivity is attributed to competition between one electron transfer, two electron transfer and Diels–Alder reaction of these sulfides with electron‐deficient acetylenes. We have proposed plausible mechanisms to account for various reactions observed by us. Copyright © 2015 John Wiley & Sons, Ltd.

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Comparative study of chemical and light induced electron-transfer reactions of some (anthracen-9-yl)methanamines is reported. Ceric ammonium nitrate was used to initiate chemically-induced electron-transfer reactions of anthracenemethanamines. Nitration at the 2-position followed by oxidation was the major pathway observed in the reaction with CAN while electron-transfer mediated C-N bond cleavage followed by dimerization was the major pathway in photochemical reactions.