Add time:08/20/2019         Source:sciencedirect.com

Publisher SummaryThe indole Grignard reagents are widely employed as intermediates in synthetic work, mainly for the introduction of substituents into the 1- or 3- positions of the indole ring system. This chapter reviews comprehensively the chemistry of the indole Grignard reagents. The chapter also discusses the reactions of the indole magnesium halides, classified according to the chemical nature of the co-reactant species. Reactions involving indole Grignard reagents, which have appeared during the past half century are also described. The ideas that have been advanced to account for the structure and reactivity of the indole Grignard reagent are also considered. The most widely used procedures for the preparation of the indole magnesium halides are described. The reactions of the indole Grignard reagents resemble those of simple aryl or alkyl magnesium halides. The chapter also discusses the various reactions associated with indole magnesium halides such as reactions with organic halogen compounds, carbonyl compounds, nitro compounds, and miscellaneous compounds. The molecular structure of indole magnesium halides suggests that they are essentially N–MgX species, with the degree of ionic character of the N–MgX bond being affected by external factors such as the polarity of the medium.

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