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Fragmentation of Homoallylic Alkoxides. Preparation of 1‐(3′‐cyclopentenyl)‐2‐alkanones from 2‐substituted bicyclo[2.2.1]hept‐5‐en‐2‐ols
Author(s) -
Snowden Roger L.
Publication year - 1983
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19830660405
Subject(s) - chemistry , heterolysis , allylic rearrangement , alkoxide , bicyclic molecule , fragmentation (computing) , medicinal chemistry , intramolecular force , protonation , bond cleavage , cleavage (geology) , ion , stereochemistry , organic chemistry , catalysis , fracture (geology) , computer science , engineering , operating system , geotechnical engineering
The potassium 2‐substituted bicyclo[2.2.1]hept‐5‐en‐2‐alkoxides derived from alcohols 2–9 at 30° in hexamethylphosphoric triamide (HMPA) afford 1‐(3′‐cyclopentenyl)‐2‐alkanones 10–19 via heterolytic C(1), C(2)‐allylic bond cleavage in the substrate alkoxide followed by intramolecular protonation of the resultant transient allylic anion.