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Tertiary Amines: History
Please note this is an old version of this entry, which may differ significantly from the current revision.
Subjects: Chemistry, Organic
Contributor: Helena Kang

Tertiary amines serve as versatile nucleophiles in organic synthesis, facilitating the formation of C-N bonds through various coupling reactions and enabling the construction of complex molecular architectures [1]. Its defining scope is the molecular transformation, structure, or mechanistic feature stated in that description; a reagent, catalyst, solvent, or processing condition is not itself the concept unless it determines that defining feature. At the molecular level, the classification depends on the identity of the participating functional groups and on the connectivity or stereochemical change that distinguishes the product or intermediate. Related variants may differ in substrate class, catalyst, or elementary pathway while retaining the same central structural criterion [2]. The term therefore has a narrower meaning than general chemical reactivity: processes that merely share a reagent, reaction condition, or product family belong to the concept only when they satisfy the same defining bond change or structural criterion. This boundary separates the concept from neighboring transformations that alter a similar functional group by a different net pathway. The description identifies the chemical class itself and does not prescribe a single experimental protocol.

  • tertiary amines
  • amine
  • nucleophile
  • coupling

Advanced Synthetic Organic Chemistry • Organic Chemistry • Chemistry • Physical Sciences

References

  1. Konrad Chojnacki; Tori Demuth; Jenna Faulkner; Ping Guo; Pushkar Bansal; Husaib Arshad; Justin English; Randall T. Peterson; Dennis Svatunek; Raphael M. Franzini; et al. Click-to-Release Reactions for Tertiary Amines and Pyridines. J. Am. Chem. Soc. 2026, 148, 3894-3908, 10.1021/jacs.5c22237.
  2. Jianke Su; Yu Guo; Chengbo Li; Qiuling Song; Difluorocarbene-induced [1,2]- and [2,3]-Stevens rearrangement of tertiary amines. Nat. Commun. 2024, 15, 1-10, 10.1038/s41467-024-49054-x.
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