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Side Reactions in Organic Synthesis (A Guide to Successful Synthesis Design) || Aliphatic Nucleophilic Substitutions: Problematic Electrophiles

✍ Scribed by Zaragoza Dörwald, Florencio

Publisher
Wiley-VCH Verlag GmbH & Co. KGaA
Year
2005
Tongue
German
Weight
1016 KB
Edition
1
Category
Article
ISBN
3527310215

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✦ Synopsis

Nucleophilic substitutions at sp 3 -hybridized carbon are among the most useful synthetic transformations, and have been thoroughly investigated [1][2][3]. The success of these reactions depends mainly on the structures of the nucleophile and electrophile, their concentration, and on the solvent and reaction temperature chosen. The structure of the electrophile in nucleophilic substitutions is of critical importance, because many unwanted side reactions result from unexpected reactivity of the electrophile.

In Scheme 4.1 the mechanisms of typical monomolecular (Sn1) and bimolecular (Sn2) nucleophilic substitutions at a neutral electrophile with an anionic nucleophile are sketched. Sn1 reactions usually occur when the electrophile is sterically 4

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