R. D. Adams, T. S. Barnard, K. Brosius
Jun 20, 1999
Citations
0
Influential Citations
11
Citations
Journal
Journal of Organometallic Chemistry
Abstract
Abstract A series of 1,3-dioxolanes have been prepared by the addition of ketones to epoxides in the presence of the catalyst [Cp*Ir(NCMe) 3 ] 2+ , Cp*C 5 Me 5 . The reactions proceed readily at 22°C and the yields are good. The following 1,3-dioxolanes: 2,2,4-trimethyl-1,3-dioxolane, 1 ; 2,2-dimethyl-4-vinyl-1,3-dioxolane, 2 ; 2,2-dimethyl-4-phenyl-1,3-dioxolane, 3 ; 2,2-diethyl-4-methyl-1,3-dioxolane, 4 ; 2,2-diethyl-4-vinyl-1,3-dioxolane, 5 ; 2,2-diethyl-4-phenyl-1,3-dioxolane, 6 were prepared from the appropriate epoxide and carbonyl compounds. An inversion of configuration at the carbon atom at the C–O bond cleavage site of the epoxide was observed to occur in the formation of the dioxolanes: R , S ,- 2,2,4,5-tetramethyl-1,3-dioxolane, 7 and a mixture of R , R - and S , S -2,2,4,5-tetramethyl-1,3-dioxolane, 8 obtained from the reactions of acetone with R , R ,-/ S , S ,-buten-2-oxide and R , S ,-buten-2-oxide, respectively.