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The Synthesis, Structural Characterisation and Chemical Manipulation of the [6+3] Cycloadduct Derived from α‐Tropolone O ‐Methyl Ether and Trimethylenemethane
Author(s) -
Crisp Antony L.,
Noble Benjamin,
Schwartz Brett D.,
Willis Anthony C.,
Coote Michelle L.,
Banwell Martin G.
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900334
Subject(s) - trimethylenemethane , tropolone , chemistry , adduct , cycloaddition , ether , bicyclic molecule , stereochemistry , undecane , medicinal chemistry , organic chemistry , catalysis
The title bicyclic system 3 , the adduct arising from the formal [6+3] cycloaddition of α ‐tropolone O ‐methyl ether ( 1 ) and trimethylenemethane ( 2 ), has been prepared and subject to single‐crystal X‐ray analysis. The chemical manipulation of adduct 3 in a range of ways is reported, including through acid‐catalysed rearrangement of the derived mono‐oxide to give the bicyclo[4.3.1]undecane 21 .