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Dramatic solvent and concentration dependence in the reaction of (anthracen‐9‐yl)methanamines with suitable electron‐deficient acetylenes
Author(s) -
Jacob Jomon P.,
Gopalakrishnan Reshma,
Mallia Rekha R.,
Vadakkan Jean John,
Unnikrishnan Perupparampil A.,
Prathapan Sreedharan
Publication year - 2014
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3351
Subject(s) - chemistry , reactivity (psychology) , solvent , electron transfer , solvent effects , organic solvent , electron , medicinal chemistry , computational chemistry , photochemistry , organic chemistry , chemical engineering , medicine , physics , alternative medicine , pathology , quantum mechanics , engineering
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.