Nucleophilic substitution of halopyridines by benzenethiolate anion  via  a radical chain mechanism | Zendy

Kondo Shuji | Zendy; Nakanishi Minoru | Zendy; Tsuda Kazuichi | Zendy

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Nucleophilic substitution of halopyridines by benzenethiolate anion via a radical chain mechanism

Author(s) -

Kondo Shuji,

Nakanishi Minoru,

Tsuda Kazuichi

Publication year - 1984

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570210466

Subject(s) - chemistry , scavenger , reactivity (psychology) , medicinal chemistry , nucleophile , radical nucleophilic aromatic substitution , substitution reaction , nucleophilic substitution , ion , electron transfer , azobenzene , photochemistry , nucleophilic aromatic substitution , radical , organic chemistry , molecule , catalysis , medicine , alternative medicine , pathology

2‐Halopyridines 1a‐d reacted with sodium thiophenoxide in DMF at 80° to afford the ipso ‐substitution products. The following relative order of reactivity was observed: 2‐iodopyridine ( 1a) ∼ 2‐bromopyridine ( 1b) ≫ 2‐chloropyridine ( 1c ) ∼ 2‐fluoropyridine ( 1d ). The reaction of 1b is inhibited by the electron scavenger azobenzene and by the radical scavenger benzoqoquinone. Furthermore, results of the reaction of 3‐bromopyridine ( 2b ) serve to rule out pyridyne mechanism. It is reasonable to suggest therefore that the reaction proceeds through the radical chain process containing one electron transfer, that is S RN 1.

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