Journal of Organic Chemistry p. 3091 - 3097 (1981)
Update date:2022-08-05
Topics:
Canonne, Persephone
Belanger, Denis
Lemay, Gilles
Foscolos, Georges B.
Carbocyclic acid anhydrides can be converted to spiro γ- and δ-lactones by addition of di-Grignard reagents in tetrahydrofuran solution.Five- and six-membered rings have been formed in one-step reactions.Possible mechanistic pathways for this reaction are discussed.The conversion of spirolactones to 1-(ω-hydroxyalkyl)cycloalkanols was accomplished by reduction with LAH to illustrate the versatility of these substances giving (after or upon treatment with tosyl chloride) the corresponding spiroethers.
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Doi:10.1016/S0031-9422(00)85452-7
(1969)Doi:10.1002/jhet.5570410420
(2004)Doi:10.1021/ic50223a044
(1981)Doi:10.1039/DT9810001010
(1981)Doi:10.1016/S0277-5387(00)84401-0
(1983)Doi:10.1007/s11164-018-3501-2
(2018)
