Alkaline hydrolysis of the cycloadduct of benzocyclobutene with 2H-pyran-2-one gives 8-hydroxy-4a,5,8,8a-tetra hydrobiphenylene-5-carboxylic acid (7) which undergoes an acid-catalysed rearrangement to the lactone of 6,9-dihydro-10-hydroxy-5,9-methano-5H-benzocycloheptene-6-carboxylic acid (4). A likely mechanism for this rearrangement is discussed.
J. W. Barton, J. A. K. Howard, M. K. Shepherd and A. M. Stringer, J. Chem. Soc., Perkin Trans. 1, 1987, 2443 DOI: 10.1039/P19870002443
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