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3 Polish Journal of Chemistry

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Reaction of cyclic allylic acetates with aliohatic alcohols in the presence of cerium(III) chloride

100%

Uzarewicz A. , Dresler R.

tom Vol. 72, nr 8

1921-1930

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.

Reduction of Epoxy Isophorone Oxime by Metal Hydrides

100%

Dresler R. , Uzarewicz A.

tom Vol. 74, nr 11

1581-1587

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.

Synthesis and Reactions of Organic Compounds with a Nitrogen Atom. Part XVII. Reactions of Acyclic and Monocyclic Chlorides with Phenylselenosodium

80%

Bąkowska-Janiszewska J. , Ścianowski J. , Uzarewicz A.

tom Vol. 75, nr 5

649-656

The reaction of neryl (3), geranyl (4), (+)-carvotanacetyl (5), (-)-carvyl (6) and perillyl (7) chlorides with phenylseleno- (1) or phenyltellurosodium (2), and then with chloramine- T afforded _,_-unsaturated toluenesulfonamides 8-11, which were reduced with sodium in liquid ammonia to allylic amines 12-15. Allylic phenyltellurides were oxidized by air to carbonyl compounds 29-31 or alcohol 28.