Observation by NMR of cationic Wheland-like intermediates in the deiodination of protected 1-iodonaphthalene-2,4-diamines in acidic media.
1-Iodonaphthalene-2,4-diamines in trifluoroacetic acid/chloroform give stable Wheland-like tetrahedral cationic species observable by NMR, through an initial intramolecular protonation. Dynamic equilibria allow proton-deuterium exchange of aromatic protons and provide a mechanism for deiodination of 1-iodonaphthalene-2,4-diamines.
Medicinal Chemistry, Department of Pharmacy and Pharmacology, University of Bath, Claverton Down, Bath, BA2 7AY, UK.
Elvis A
EA
Twum
Timothy J
TJ
Woodman
Wenyi
W
Wang
Michael D
MD
Threadgill
D002412:Cations / Q000737:chemistry; D002725:Chloroform / Q000737:chemistry; D003959:Diamines / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry*
D002412:Cations; D003959:Diamines; D009281:Naphthalenes; D002725:Chloroform; D014269:Trifluoroacetic Acid