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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

2001

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.

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

2000

Vol. 74, nr 8

1079-1083

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

2000

Vol. 74, nr 6

777-783

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).

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

1999

Vol. 73, nr 11

1791-1796