Gv. Shustov et al., CHIROPTICAL PROPERTIES OF C2-SYMMETRICAL N-HALOAZIRIDINES - CHIRAL RULES FOR THE N-HALOAZIRIDINE CHROMOPHORE, Journal of the American Chemical Society, 115(22), 1993, pp. 10267-10274
N-Chloro (a) and N-bromo (b) derivatives of C2-symmetric aziridines (2
S,3S)-1-halogen-2,3-dimethylaziridines 1a,b and 2S,3S)-1-halogen-2,3-b
is(alkoxycarbonyl)aziridines 2a,b and 3a,b were obtained. Haloaziridin
es 1a,b are an example of the ''pure'' N-haloaziridine chromophore whi
ch has the first Cotton effect (CE) in the region of 260-300 nm. A qua
drant rule which connects the first CE sip with the stereochemical env
ironment of the chromophore is offered. Haloaziridinecarboxylic esters
are a specific case of the N-haloaziridine chromophore. The second CE
sign at 220-230 nm in the CD spectra of these compounds obeys a rever
se quadrant rule.