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Azetidiniums: Ring‐Expansion to Pyrrolidines, Piperidines, Azepanes, and Azocanes
Author(s) -
Masson Guillaume,
Gomez Pardo Domingo,
Cossy Janine
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000794
Subject(s) - nucleophile , chemistry , ring (chemistry) , bicyclic molecule , stereochemistry , organic chemistry , catalysis
The 4‐membered ring in bicyclic azetidiniums, e.g. 1‐azabicyclo[2.n.0]alkanes ( n = 1–4), can be efficiently transformed to larger rings. This minireview focuses on the ring‐expansion of these azetidiniums to five‐ and eight‐membered nitrogen containing heterocycles (pyrrolidines, piperidines, azepanes and azocanes). The ring‐expansion is induced by nucleophiles which can be internal nucleophiles (leaving groups), or external nucleophiles.