Nucleophilic Aromatic Substitution of Hydrogen

Nucleophilic aromatic substitution in carbo- and heteroaromatic systems is a subject of considerable interest to chemists. This book uniquely addresses the systematic analysis of a vast range of nucleophilic substitutions of aromatic hydrogen.

• This text provides coverage of:
• Nucleophilic displacement of hydrogen (the S N/H reactions) in pi-deficient aromatics, such as nitroarenes, arene-metal complexes, and the like.
• Nucleophilic displacement of hydrogen in heterocyclic substrates such as pyridines, their aza and benzo analogs, pyrylium and thiapyrylium cations, and other heterocycles
• Mechanisms for the S N/H reactions (S N/H(AE), vicarious nucleophilic substitutions, and radical S N/H substitutions

Researchers in organic chemistry, pharmaceutical (industrial) chemistry, and materials chemistry; graduate and post-graduate students in organic synthesis.

Introduction. Nucleophilic Substitution of Hydrogen in Arenes: Unactivated Arenes. Arene-Metal Complexes. Nitroarenes. Electrochemical S H/N [H over N] Reactions. Tropylium Salts and Other Non-Benzenoid Compounds. Intramolecular S H/N Reactions and Rearrangements Accompanied by S H/N Substitution.

Nucleophilic Substitution of Hydrogen in Heteroaromatics: Azines. Azaaromatic Substrates Containing Quaternary Nitrogen. Pyrylium and Thiopyrylium Cations. Five-Membered Heterocycles. Electrochemical S H/N Reactions. Intramolecular S H/N Reactions in Heteroaromatics.

Reactivity of Arenes and Hetarenes and Mechanisms of the S H/N Reactions: The Addition–Elimination S H/N(AW) Mechanism. The Elimination–Addition S H/N(EA) Mechanism. The S H/N(ANRORC) Mechanism.

References. Subject Index.