Observation by NMR of cationic Wheland-like intermediates in the deiodination of protected 1-iodo-naphthalene-2,4-diamines in acidic media

Elvis A Twum; Timothy J Woodman; Wenyi Wang; Michael D Threadgill

doi:10.1039/C3OB41386A

Observation by NMR of cationic Wheland-like intermediates in the deiodination of protected 1-iodo-naphthalene-2,4-diamines in acidic media

Elvis A Twum, Timothy J Woodman, Wenyi Wang, Michael D Threadgill

Department of Life Sciences

Shandong University

Research output: Contribution to journal › Article › peer-review

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Abstract

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 iodo-napthalene-2,4-diamines.

Original language	English
Pages (from-to)	6208-6214
Journal	Organic and Biomolecular Chemistry
Volume	11
Issue number	36
Early online date	7 Aug 2013
DOIs	https://doi.org/10.1039/C3OB41386A
Publication status	Published - 2013

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title = "Observation by NMR of cationic Wheland-like intermediates in the deiodination of protected 1-iodo-naphthalene-2,4-diamines in acidic media",

abstract = "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 iodo-napthalene-2,4-diamines.",

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AU - Woodman, Timothy J

AU - Wang, Wenyi

AU - Threadgill, Michael D

PY - 2013

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N2 - 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 iodo-napthalene-2,4-diamines.

AB - 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 iodo-napthalene-2,4-diamines.

UR - http://dx.doi.org/10.1039/C3OB41386A

U2 - 10.1039/C3OB41386A

DO - 10.1039/C3OB41386A

M3 - Article

SN - 1477-0520

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SP - 6208

EP - 6214

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 36

ER -

Observation by NMR of cationic Wheland-like intermediates in the deiodination of protected 1-iodo-naphthalene-2,4-diamines in acidic media

Abstract

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