5110-77-0Relevant articles and documents
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Kadaba et al.
, p. 1431,1433 (1960)
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PEG400-enhanced synthesis of gem-dichloroaziridines and gem-dichlorocyclopropanes via in situ generated dichlorocarbene
Song, Qing-Wen,Yu, Bing,Liu, An-Hua,He, Ying,Yang, Zhen-Zhen,Diao, Zhen-Feng,Song, Qing-Chuan,Li, Xue-Dong,He, Liang-Nian
, p. 19009 - 19014 (2013/10/22)
PEG400 is employed as an efficient phase transfer catalyst for the cycloaddition reaction of imines with dichlorocarbene, which is generated in situ from chloroform and sodium hydroxide, to give gem-dichloroaziridines in moderate to excellent yields at ambient temperature. This protocol is also extended to the synthesis of cyclopropanes from a variety of alkenes. In this study, PEG400 behaves as a phase transfer reagent thanks to its ability to coordinate with alkali metal cations. Notably, the one-pot synthesis of gem-dichloroaziridines from benzaldehyde and aromatic amines has also been successfully performed. The in situ generated acid, derived from CO2 and H2O, can also be effectively applied to promote the amide synthesis via the gem-dichloroaziridine pathway. The application of the gem-dichlorocyclopropane as a platform chemical is also briefly demonstrated, to afford the 2-phenylacrylaldehyde derivative via a ring-opening reaction. The Royal Society of Chemistry 2013.
1,3-DIARYL-2,2-DIHALOAZIRIDINES IN NITRATION AND BROMINATION REACTIONS
Khlebnikov, A. F.,Kostikov, R. R.
, p. 739 - 744 (2007/10/02)
In the nitration of 3-(4-nitrophenyl)-1-phenyl-2,2-dichloroaziridine in acetic acid, 1-(o- and p-nitrophenyl)-derivatives are formed in a 35:65 ratio. 1,3-Diphenyl-2,2-dichloroaziridine undergoes opening of the three-membered ring under the same conditions, forming a mixture of o- and p-nitroanilides and 2-nitro-4-chloroanilides of 2-acetoxy (or 2-chloro)-2-phenylacetic acids.The bromination of 3-(4-nitrophenyl)-1-phenyl-2,2-dichloroaziridine in aqueous acetic acid leads to 1-(4-bromophenyl)-3-(4-nitrophenyl)-2,2-dichloroaziridine, while in a mixture of acetic acid and acetic anhydride it leads to the anilide of 2-bromo-2-phenylacetic acid and 2-bromo-N-(2,4-dibromophenyl)-1-(4-nitrophenyl)-2,2-dichloroethylamine.