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

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

Polish Journal of Chemistry

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2001

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Vol. 75, nr 5

649-656

EN

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.

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Synthesis and Reactions of Organic Compounds with a Nitrogen Atom : Part XVI. Reactions of (-)-4Chloro-3(10)-carene and (+)-10-Chloro-3-carene with Phenyltelluro- and Phenylselenosodium

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

Polish Journal of Chemistry

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2000

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Vol. 74, nr 8

1079-1083

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Reduction of Epoxy Isophorone Oxime by Metal Hydrides

Dresler R., Uzarewicz A.

Polish Journal of Chemistry

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2000

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Vol. 74, nr 11

1581-1587

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.

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Reaction of (+)-3-Carene and (+)-2-Carene with t-Butyl Hypochlorite or N-Chlorsuccinimide in the Presence of Free Radical Catalysts

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

Polish Journal of Chemistry

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2000

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Vol. 74, nr 6

777-783

EN

Allylic chlorination of (+)-3carene (1) gave (-)-trans-4-chloro-3(10)-carene (2), (+)-10-chloro-carene (4) and 3,4-dichlorocarene (5). Chlorination was done by two methods: with t-butyl hypochlorite or N-chlorsuccinimide in the presence of catalytic amount of alpha, alpha'-azobisisobutylonitrile or benzoyl peroxide, UV irradiation and silica gel. Chlorination of (+)-2-carene (7) using these methods gave p-cymene (8), 1-isopropylene-4-methylbenzene (9) and dipentene (10).

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Synthesis and Reactions of Organic Compounds with a Nitrogen Atom : Part XV : Reactions of (+)-3-Chloro-2(10)-pinene and (-)-10-Chloro-2-pinene with Phenyltelluro- and Phenylselenosodium

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

Polish Journal of Chemistry

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1999

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Vol. 73, nr 11

1791-1796

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Synthesis and reaction of organic compounds with a nitrogen atom. Part XII. Reaction of aplha- and beta-pyronene with bis (p-toluenesulfonyl)selenodiimide

Ścianowski J., Uzarewicz A.

Polish Journal of Chemistry

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1998

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Vol. 72, nr 1

93-98

EN

Toluenesulfonamidation of alpha-pyronene (1,5,5,6-tetramethyl-1,3-cyclohexadiene) afforded two toluenesulfonamides: N,N'-(1',5',5',6'-tetramethyl-3'-cyclohexan-1',2'-diyl)ditoluenesulfonamide (9) and 4-methyl-N-(4',5',6',6'-tetramethyl-2',4'-cyclohexadien-1'-yl)benzensulfonamide (12). Toluenesulfonamidation of beta-pyronene (1,2,6,6-tetramethyl-1,3-cyclohexadiene) gave N,N'-(3',4',5',5'-tetramethyl-3'-cyclohexen-1',2'-diyl)ditoluenesulfonamide (16). Allylic mono- and ditoluenesulfonamides 9, 12, 16, were reduced by sodium in liquid ammonia to corresponding allylic mono- and diamines 17, 18 i 19.

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

Uzarewicz A., Dresler R.

Polish Journal of Chemistry

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1998

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Vol. 72, nr 8

1921-1930

EN

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.

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Reaction of allylic alcohols with aliphatic alcohols in the presence of cerium(III) chloride. Part II

Uzarewicz A., Dresler R., Ścianowski J.

Polish Journal of Chemistry

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1998

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Vol. 72, nr 4

710-718

EN

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 .