ISSN:
0899-0042
Keywords:
Circular dichroism
;
helicity rule
;
X-ray structure determination
;
ultraviolet spectra
;
n - π* and π - π* bands
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Chiroptical properties of a series of 3 and/or 4-heterosubstituted 2(5H)-furanones were investigated with respect to correlation with absolute configuration. The n - π* and π - π* Cotton effects have been assigned on the basis of comparison with the UV spectra in solvents of varying polarity. It is demonstrated that the n - π* transition in 4-amino substituted 2(5H)-furanones appears at shorter wavelength with respect to the π - π* transition. With the exception of 4-pyrrolidino and 4-benzylamino substituted 2(5H)-furanones, other heterosubstituted 2(5H)-furanones follow the butenolide configurational rule (Gawronski et al. J. Org. Chem. 61:1513-1515, 1996). Absolute configuration of 2(5H)-furanone derivatives can also be assigned according to the sign of the Cotton effect (of unknown origin) at 200-230 nm. The structure of four representative sulfur and nitrogen substituted 2(5H)-furanones has been analyzed by X-ray diffraction. The results indicate planarity of the furanone ring and extended conjugation in 4-amino substituted 2(5H)-furanones. Chirality 9:537-544, 1997. © 1997 Wiley-Liss, Inc.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
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