Reduction of Epoxy Isophorone Oxime by Metal Hydrides

• Autorzy: Dresler R. , Uzarewicz A.
• Języki publikacji: PL

Abstrakty

EN

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.

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2000
• Tom: Vol. 74, nr 11
• Strony: 1581--1587
• Opis fizyczny: Bibliogr. 13 poz., rys.

Twórcy

autor

Dresler R.

autor

Uzarewicz A.

• Faculty of Chemistry, Nicolaus Copernicus University, 7 Gagarin Street, 87-100 Toruń, Poland