Trapping of the Dichlorocarbonyl Oxide Using a Chiral (Salen)Mn(III) Complex

Bulletin of the Korean Chemical Society

Volumn 18, Issue 8, 1997, Pages 796-798

  Lee, Nam Ho ^a   Balk, Jong Seok ^a   Han, Sung Bin ^a  

^a Jeju National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0642273362     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

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25. The enantiomeric excess of the compound 4 was determined to be zero, which implies that the catalyst 2 was not involved in cyclopropanation process. For the reference of the related metalloporphyrin-mediated cyclopropanation reaction, see Ziegler, C. J.; Suslick, K. S. J. Am. Chem. Soc. 1996, 118, 5306.
26. We could not exclude the possibility of dichlorodioxirane, the cyclic isomer of 1a. involving as the active oxidant. However, the isomerization of carbonyl oxide to the corresponding dioxirane was reporeted to have relatively high activation energy barrier. For the reference, see Hull, L. A. J. Org. Chem. 1978, 43, 2780.
27. 4NBr (0.04 mmol), imidazole (1 mmol) and sodium hydroxide (6 M, 10 mL) in the presence of the catalyst (S,S)-2 (0.1 mmol) was bubbled the oxygen gas for 12 h at room temperature. After the phases were separated, the organic layer was washed with brine solution and dried with anhydrous sodium sulfate. After being concentrated, the mixture was analyzed by GC and GC-MSD spectroscopy or purified by flash column chromatography.
28. 2 as the oxidant.
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