Uncatalyzed conjugate additions of diorganozincs in N- methylpyrrolidinone

Tetrahedron Letters

Volumn 37, Issue 26, 1996, Pages 4495-4498

  Reddy, Ch Kishan ^a   Devasagayaraj, A ^a   Knochel, P ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; 2 PYRROLIDONE DERIVATIVE; NITRILE; NITRO DERIVATIVE; ORGANIC COMPOUND; ZINC DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; CONJUGATION; STOICHIOMETRY; STRUCTURE ANALYSIS;

EID: 0030600161     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00915-X     Document Type: Article

References (33)

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33. 2Zn (2 mL, 20 mmol) was added. The reaction mixture was stirred for 10 min at 0 °C and for 20 min at rt. It was again cooled to 0 °C and the solvents were removed as described above. The resulting zinc reagent (1e) was diluted in THF (3 mL) and was ready to use. A 50 mL three-necked flask was charged with THF (2 mL) and NMP (3 mL) and was cooled to -30 °C. 2-Cyclopenten-1-one (410 mg, 5 mmol) and TMSCl (500 mg, 5 mmol) were added followed by bis(myrtanyl)zinc (1e) (3 mL of the above prepared solution, 5 mmol). The resulting reaction mixture was stirred for 3 h at -30 °C and was poured into an aqueous 10 % HCl solution (20 mL) in THF (20 mL), stirred for 15 min and was worked up as usually. After evaporation of the solvents, the crude residue was purified by flash chromatography (hexane:ether = 95:5) providing 3-myrtanylcyclopentanone (3h; 869 mg, 79 %) as a colorless oil.