Nucleophilic aromatic substitution reactions promoted by aryl and heteroaryl amine nitranions

Nucleophilic aromatic substitution reactions promoted by aryl and heteroaryl amine nitranions Full article

Journal

New Journal of Chemistry
ISSN: 1144-0546

Output data

Year: 1998, Volume: 22, Number: 1, Pages: 71-74 Pages count : 4 DOI: 10.1039/a706744e

Authors

Landini D. ¹ , Maia A. ¹ , Secci D. ² , Vlasov V.M. ³ , Os'kina I. ³

Affiliations

1	Centra CNR, Dipartimento di Chimica Organica e Industriale dell'Università, Via Golgi 19, I-20133 Milano, Italy
2	Dipartimento Fannaco Chimico Tecnologico dell'Università, Via Ospedale 72, I-09124 Cagliari, Italy
3	nstitute of Organic Chemistry, Russian Academy of Sciences, Siberian Division, 9, Lavrentiev Ave., 630090 Novosibirsk, Russian Federation

The nucleophilic substitution reaction of chlorine in 4-chloronitrobenzene by N-anions from aryl and heteroarylamines 1-4, to give the corresponding diarylamines, has been studied in solvents of different polarity (toluene and DMSO). The reactivity of these nitranions is found to be two orders of magnitude higher in DMSO. Such a difference is attributed to the different reacting species lion pairs and free ions in toluene and DMSO, respectively). The beta(Nu) values obtained (0.31 and 0.26), very similar and relatively low, suggest a moderate extent of charge transfer from nucleophile to substrate in the transition state of both systems.

Landini D. , Maia A. , Secci D. , Vlasov V.M. , Os'kina I.
Nucleophilic aromatic substitution reactions promoted by aryl and heteroaryl amine nitranions
New Journal of Chemistry. 1998. V.22. N1. P.71-74. DOI: 10.1039/a706744e WOS Scopus РИНЦ

Web of science	WOS:000073569200012
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