Journal of the Chemical Society. Perkin transactions I p. 2848 - 2863 (1981)
Update date:2022-08-02
Topics:
Adlington, Robert M.
Barrett, Anthony G. M.
Using the Shapiro reaction, the title compounds were prepared in 'one pot' from the consideration of two ketones, or an aldehyde and a ketone, with carbon dioxide.For example, acetone 2,4,6-tri-isopropylbenzenesulphonylhydrazone was treated in sequence with n-butyl-lithium (-50 deg C), acetone (-50 deg C), n-butyl-lithium (-78 to 0 to -78 deg C), carbon dioxide (-78 deg C), and trifluoroacetic acid (25 deg C) to give 5,5-dimethyl-3-methylenetetrahydrofuran-2-one.The reaction was extended to prepare derivatives of 3-methylenetetrahydropyran-2-one and 3,5-dimethylenetetrahydrofuran-2-one.
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