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Aromatic Substitution

2016; Linguagem: Inglês

10.1002/9781118707838.ch5

1935-0139

Michael R. Crampton,

Asymmetric Hydrogenation and Catalysis

This chapter discusses the importance of transition-metal-catalysed reactions continues to increase, and their uses in substitutions involving carbon-carbon bond formation. It focuses on traditional mechanisms involving bond formation to oxygen, nitrogen, sulfur, and the halogens. An examination of the enthalpies of complete hydrogenation of the rings of monosubstituted benzenes shows that the values reflect the electrophilic reactivities of the arenes. The electrophilic reactivity of linear acenes has been investigated using interaction energy potentials with copper(I) as a model electrophile; reactivity was shown to increase with length of the acene. The alpha effect, the enhanced reactivity of nucleophiles with a lone pair of electrons on an adjacent center, has been investigated in reactions with substituted phenyl-phenyl carbonates inwater/ dimethyl sulfoxide (DMSO) solvent. Carbon-carbon bond formation is one of the fundamental processes of organic chemistry, and aromatic substitution has been revolutionized by the use of transition metal catalysts.