The acid-catalysed lactonisation of the norborn-5-en-2-ylacetic acids affords a mixture of 2-exo-hydroxynorborn-7-syn-ylacetic acid δ-lactone and 2-exo-hydroxynorborn-3-exo-ylacetic acid γ-lactone. The latter appears to be the thermodynamically more stable lactone, and is the predominant product under extended reaction times. Product formation may be rationalised via a series of equilibrating norbornyl cations.
D. I. Davies and M. D. Dowle, J. Chem. Soc., Perkin Trans. 1, 1978, 227 DOI: 10.1039/P19780000227
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