Butane-2,3- (la), pentane-2,4- (Ib) and hexane-2,5-dione (Ic) react with Bu-2(CH2=CHCH2)SnCl in the presence of water to give monoallylated keto-ols (2a, 2b) and/or diallylated diols (3a, 3b, 3c), this depending upon the employed molar ratio [diketone]/[allyltin chloride]. Bu(CH2=CHCH2)SnCl2 reacts with neat Ic in a one-pot synthesis to give mixtures of heterocyclic compounds: 2,5-diallyl-2,5-dimethyltetrahydrofuran (4), and 3-chloro-1,5-dimethyl-8-oxabicyclo [3,2,1] octane (5). Compound 4 is also obtained in high yield from the corresponding diol 3c by cyclodehydration promoted by RSnCl3 (R = Me and Bu)
Allylstannation of alfa-, beta- and gamma-diketones mediated by allyldibutyltin halides: Bu2(2CH=CHCH2)SnCl and Bu(2CH=CHCH2)SnCl2
MARTON, DANIELE;
1997
Abstract
Butane-2,3- (la), pentane-2,4- (Ib) and hexane-2,5-dione (Ic) react with Bu-2(CH2=CHCH2)SnCl in the presence of water to give monoallylated keto-ols (2a, 2b) and/or diallylated diols (3a, 3b, 3c), this depending upon the employed molar ratio [diketone]/[allyltin chloride]. Bu(CH2=CHCH2)SnCl2 reacts with neat Ic in a one-pot synthesis to give mixtures of heterocyclic compounds: 2,5-diallyl-2,5-dimethyltetrahydrofuran (4), and 3-chloro-1,5-dimethyl-8-oxabicyclo [3,2,1] octane (5). Compound 4 is also obtained in high yield from the corresponding diol 3c by cyclodehydration promoted by RSnCl3 (R = Me and Bu)
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