The title reaction has been used to prepare nine-membered lactones commencing from 2-vinyltetrahydrofurans and dichloroketene; the resulting Δ5-dichlorolactones are exclusively trans but dechlorination using Bu3SnH–AlBN (azoisobutyronitrile) achieves concomitant isomerisation to give the cis-unsaturated lactones.
M. R. Kling, G. A. McNaughton-Smith and R. J. K. Taylor, J. Chem. Soc., Chem. Commun., 1993, 1593 DOI: 10.1039/C39930001593
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