METAMECONINE AS A MODEL COMPOUND IN THE STUDY OF AROMATIC REACTIONS

1962 ◽  
Vol 40 (12) ◽  
pp. 2402-2408 ◽  
Author(s):  
S. Safe ◽  
Marjorie Allen ◽  
R. Y. Moir
Keyword(s):  
Physical Properties ◽  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Model Compound ◽  
Substitution Reactions ◽  
Main Interest ◽  
Nucleophilic Substitution Reactions ◽  
Special Character ◽  
Methylene Group

Previous work had shown the somewhat unexpected course of nitration, bromination, and demethylation reactions of metameconine and its derivatives. The discovery that metameconine could easily be dinitrated enabled us to bring to light equally interesting results in the relative rates of reduction of the nitro groups, in the course of certain nucleophilic substitution reactions, in the activation of the methylene group, and in certain physical properties. Much of the work, past and present, now holds as its main interest the somewhat special character of a nitro group in the 7-position.

Studies on some selective and competitive substitution reactions of cyclopentadienyliron complexed chloronitrobenzenes with amines as nucleophiles

1989 ◽  
Vol 67 (10) ◽  
pp. 1618-1623 ◽  
Author(s):  
Alaa S. Abd-El-Aziz ◽  
Adam Piórko ◽  
Choi Chuck Lee ◽  
Ronald G. Sutherland
Keyword(s):  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Major Product ◽  
Substitution Reactions ◽  
Iron Cation ◽  
Nucleophilic Substitution Reactions ◽  
Inductive Effects ◽  
Chloro Group ◽  
Selective Displacement

Nucleophilic substitution reactions of the (η6-o-, -m-, or -p-chloronitrobenzene)(η5-cyclopentadienyl)iron cation (2a, 2b, or 2c, respectively) with aniline, n-butylamine, or pyrrolidine as nucleophile were investigated. It was found that only selective displacement of the nitro group occurred for reactions with aniline. For reaction with n-butylamine or pyrrolidine, o-isomer 2a resulted in the selective displacement of only the chloro group, giving rise to the (η6-o-n-butylaminonitrobenzene)(η5-cyclo-pentadienyl)iron cation (5a) or the (η6-o-nitro-N-pyrrolidinylbenzene)(η5-cyclopentadienyl)iron cation (7a), respectively. With the m- or p-isomer 2b or 2c, reaction with n-butylamine or pyrrolidine gave a mixture of substitution products from competitive displacements of both chloro and nitro groups, the major product from the m-isomer being derived from displacement of the chloro group while the major product from the p-isomer resulted from displacement of the nitro group. Possible interpretations of these results on the basis that the basicity of the nucleophile and the combined inductive effects of the nitro and chloro substituents would play important roles are presented. Keywords: (η6-o-, -m-, and -p-chloronitrobenzene)(η5-cyclopentadienyl)iron cations, nucleophilic substitution reactions, aniline, n-butylamine, pyrrolidine.

The unexpected reactivity of 9-iodo-nido-carborane: from nucleophilic substitution reactions to the synthesis of tricobalt tris(dicarbollide) Na[4,4′,4′′-(MeOCH2CH2O)3-3,3′,3′′-Co3(μ3-O)(μ3-S)(1,2-C2B9H10)3]

2021 ◽  
Vol 50 (7) ◽  
pp. 2671-2688
Author(s):  
Marina Yu. Stogniy ◽  
Sergey A. Anufriev ◽  
Akim V. Shmal'ko ◽  
Sergey M. Antropov ◽  
Aleksei A. Anisimov ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reactions ◽  
Nucleophilic Substitution Reactions

An unusual reactivity of 9-iodo-nido-carborane [9-I-7,8-C2B9H11]− towards nucleophiles under strong basic conditions was revealed.

Sign in / Sign up

Export Citation Format

Share Document