Modern Nucleophilic Aromatic Substitution by Francois Terrier

By Francois Terrier

Content material:
Chapter 1 The SNAr Reactions: Mechanistic features (pages 1–94):
Chapter 2 constitution and Reactivity of Anionic ??Complexes (pages 95–162):
Chapter three The Superelectrophilic size in SNAr and similar ??Complexation procedures (pages 163–203):
Chapter four artificial points of Intermolecular SNAr Reactions (pages 205–278):
Chapter five Intramolecular SNAr Reactions (pages 279–336):
Chapter 6 Nucleophilic fragrant Substitutions of Hydrogen (pages 337–422):
Chapter 7 different SNAr Substitution Pathways (pages 423–463):

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121]). 4 O N N N 35 36 1 The SN Ar Reactions: Mechanistic Aspects systems. 2) [137]. The ratio kArS− /kMeO− depends also on the substrate, being greater for 1-L-2,4-dinitrobenzenes than for 1-L-4-nitrobenzenes or for 2L-6-nitrobenzothiazoles. Attempts to correlate changes in reactivity with basicity and polarizability effects through multiparameter relationships have been made by Bartoli and Todesco [137]. 2 Ritchie and Mayr’s Scales Among various attempts to correlate nucleophilic reactivities in SN Ar reactions, the work by Ritchie is worth mentioning.

The absence of hydrogen in the reactivity sequence above is a very important feature. Because of the very low anionic stability of a departing H− anion (pK a ≈ 36) [145], it can be estimated that SN Ar displacements of hydrogen are very endothermic and have transition states for C–H bond breaking that are too high in 29 30 1 The SN Ar Reactions: Mechanistic Aspects energy to be kinetically accessible. Accordingly, nucleophilic additions to activated CH ring positions will normally stop at the intermediate σ-complex [3, 8].

2) with a series of π-excessive aromatic or heteroaromatic substrates (indoles, azulene, pyrroles) has shown that SN Ar substitutions in which the addition of the nucleophile is rate limiting, are well described by Eq. 17) [126]. 8). A more elaborated discussion of the importance of Eq. 17) in defining the concept of superelectrophilicity in SN Ar and σ-complexation processes is given in Chapter 2. 8 Determination of the electrophilicity (E) of 7-chloro-4,6dinitrobenzofuroxan (DNBF-Cl) through application of Eq.

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