Nucleophilic Substitution Reactions of 1-Halogeno-4-COR-2-nitrobenzenes and 1-Halogeno-6-COR-2-nitrobenzenes with Sodium Benzenethiolate and Piperidine. Can an "Inverted Built-in Solvation" Be Responsible for the Peculiar Activation by an o-Carboxamido Group in SNAr Reactions with an Anionic Nucleophile?

Journal of Organic Chemistry

Volumn 62, Issue 10, 1997, Pages 3093-3097

  Arnone, Caterina ^a   Consiglio, Giovanni ^a   Frenna, Vincenzo ^b   Spinelli, Domenico ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF PALERMO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001169856     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961040h     Document Type: Article

References (22)

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2. Noto, R.; Frenna, V.; Consiglio, G.; Spinelli, D. J. Chem. Res., Synop. 1991, 270-271; J. Chem. Res., Miniprint 1971, 2701-2710.
3. 2 makes the first group more able to help the negative charge delocalization.
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12. It must be noted that all of the ortholpara ratios are lower than unity, indicating the occurrence of a significant kinetic primary steric effect (e.g., see: Miller, J. Aromatic Nucleophilic Substitution; Elsevier: Amsterdam, 1968; pp 95 and 350 and references therein) in the ortho-isomers because of the 2,6-disubstitution.
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