Abstract
It is fair to say that the single reaction that has received the greatest attention of organic chemists is nucleophilic substitution in aliphatic systems. The reaction is of enormous synthetic utility, and a seemingly bewildering number of facts and observations had accumulated before systematic efforts at unraveling the puzzle by mechanistic studies, most notably by Christopher K. Ingold and E. D. Hughes in England, met with any real success.1It is now possible to predict the course of nucleophilic substitution reactions with reasonable precision, and to tailor experimental conditions to maximize conversion to desired products by employing the mechanistic principles that have been set forth on the basis of these studies. There still remain, however, important details that are of current interest, as will become evident in this chapter.
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Carey, F.A., Sundberg, R.J. (1977). Nucleophilic Substitution. In: Advanced Organic Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-9792-2_5
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DOI: https://doi.org/10.1007/978-1-4613-9792-2_5
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