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Interconversion of cis ‐ and trans ‐Fused Oxabicyclo[5.2.0]nonan‐2‐ones
Author(s) -
Schmidt Kerstin,
Margaretha Paul
Publication year - 2011
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.201100203
Subject(s) - chemistry , alkene , moiety , ene reaction , diastereomer , irradiation , stereochemistry , medicinal chemistry , organic chemistry , catalysis , physics , nuclear physics
On irradiation (350 nm) in the presence of alkenes (2,3‐dimethylbut‐2‐ene, 1,1‐dimethoxyethene, and 2,4,4‐trimethylpent‐1‐ene), benzoxepinone 1 and dioxepinone 2 are converted into mixtures of cis ‐ and trans ‐fused oxabicyclo[5.2.0]nonan‐2‐ones. Their relative thermodynamic stabilities (as reflected by the observed diastereoisomer ratios after equilibration with basic alumina) depend on the substitution pattern of the alkene moiety.