Nucleophilic Aromatic Substitution of Hydrogen
Academic Press, Dec 2, 2012 - Science - 367 pages
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
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CHAPTER 3 NUCLEOPHILIC SUBSTITUTION OF HYDROGEN IN HETEROAROMATICS
CHAPTER 4 REACTIVITY OF ARENES AND HETARENES AND MECHANISMS OF THE SHN REACTIONS
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acetic acid acridine added addition adduct alkyl ammonia aniline anion aqueous arenes arnination aryl arylamines atom auxiliary group azine azinium benzene carbanions cation Chem Chemistry Chichibabin amination Chim chloride chromatography compounds cyanide displacement of hydrogen DMSO ether evaporated Example extracted ﬁltered ﬁrst formation Geterotsikl Grignard reagents Hamana heteroaromatic Heterocycl hydrogen hydroxide intermediate iodide isoquinoline Khim kinetic liquid ammonia Makosza mechanism melting point methanol methyl Minisci mmol N-oxide naphthalene nitro group nitroarenes nitrobenzene nucleofugal nucleophilic aromatic substitution nucleophilic displacement o-adducts obtained ortho oxidation perchlorate Perkin Trans phenyl phenyl sulfone Plas potassium amide potassium permanganate presence proton pyrazine pyridine pyridine pyridine pyridine ring quinoline Quinoline N-oxide radical react reaction mixture reactivity reagents reﬂux regioselectivity room temperature salts sodium Soedin solution solvent substitution of hydrogen Synthesis Table tetraﬂuoroborate Tetrahedron Lett V.N. Charushin vicarious nucleophilic substitution Yield References yields Scheme