Nucleophilic Substitution Reactions in Benzo[C][1,8]naphthyridines. II.

1990 ◽  
Vol 43 (8) ◽  
pp. 1469 ◽  
Author(s):  
P Cherubim ◽  
LW Deady
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reactions ◽  
Nucleophilic Substitution Reactions ◽  
Chloro Group ◽  
Nitrogen Nucleophiles

3-Chloro-1-methyl-6-(p- methylphenoxy ) benzo [c][1,8] naphthyridine has been prepared, the reactions with various nitrogen, oxygen and sulfur nucleophiles studied, and the results compared with those for the 1- chloro-3-methyl isomer. The 6-position was more reactive for oxygen and nitrogen nucleophiles, so much so that an initially added 6-NHR group was displaced by a second R′NH2 nucleophile at least as readily as was the 3-chloro group. With p- chloro ( thiophenol ), however, the 3-chloro group was preferentially displaced.

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.

Reactions of ethyl 4-bromo-3-(2-furyl)-2-butenoate with nitrogen nucleophiles

1981 ◽  
Vol 46 (6) ◽  
pp. 1513-1517 ◽  
Author(s):  
Katarína Špirková ◽  
Jaroslav Kováč ◽  
Ivan Horsák ◽  
Miloslava Dandárová
Keyword(s):  
Nucleophilic Substitution ◽  
Nmr Spectra ◽  
Substitution Reactions ◽  
Nucleophilic Substitution Reactions ◽  
H Nmr ◽  
Nitrogen Nucleophiles

Nucleophilic substitution reactions of ethyl 4-bromo-3-(2-furyl)-2-butenoate with nitrogen nucleophiles are described. UV, IR, and 1H NMR spectra of the prepared substances have been interpreted.

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.

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