Epoxy isophorone oxime (1) is reduced with LiAlH4/CeCl3/THF or NaBH4/MoO3/MeOH to a mixture of t-3-amino-1,5,5-trimethyl-r-1-cyclohexanol (2) and c-3-amino-1,5,5-trimethyl-r-1-cyclohexanol (3), 39:61 and 67:33, respectively. The reduction of 1 with NaBH4 or LiAlH4 affords a mixture of isomeric 3,5,5-trimethyl- 3-hydroxycyclohexan-1-one oximes 4 and 5 (syn:anti 60:40 and 44:56, respectively). The reduction of 1 with NaBH4/CeCl37H2O/ROH or CeCl37H2O/ROH (R = Me, Et, n-Pr) results in the nucleophilic opening of the epoxide ring to give 2-alkoxy-3-hydroxy derivatives 6a–c, 7a–c, and symmetric ethers 8 and 9. When 1 reacts with CeCl37H2O/t-BuOH only 8 and 9 are formed.
The reaction of selected allylic acetates with methanol, ethanol, n-propyl alcohol, isopropyl alcohol and tert-butyl alcohol in the presence of catalytic amounts of cerium(III) chloride are described. Allylic alkyl ethers, bis-allylic ethers and 1,3-dienes were obtained depending on the structure of the acetates.
The reaction of selected allylic alcohols with methanol, ethanol, n-propanol, isopropanol and tert-butanol in the presence of catalytic amounts of cerium(III) chloride are described. Allylic alkyl ethers, bis-allylic ethers and 1,3-dienes were obtained depending on the structure of the reacting alcohols .
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.