Abstract:
:Planar 2(5H)-furanones substituted at C4 with a chiral pyrrolidinyl group show CD spectra which are apparently due to the distortion of the C4-N1 bond of sp2 character from the plane defined by the 2(5H)-furanone ring atoms and/or due to the presence of substituents in the pyrrolidine ring. This is a new, previously not encountered structural factor determining the chiroptical properties of 2(5H)-furanones and emerging from the analysis of X-ray diffraction data and quantum mechanical DFT computations. In the presence of a C5 pseudoaxial substituent in the furanone ring, the sign of the furanone n-pi* and pi-pi* transition Cotton effects is determined primarily by the previously postulated allylic helicity rule.
journal_name
Chiralityjournal_title
Chiralityauthors
Gawroński J,Gawrońska K,Kwit M,Kacprzak K,Rychlewska Udoi
10.1002/chir.20059subject
Has Abstractpub_date
2004-08-01 00:00:00pages
405-13issue
7eissn
0899-0042issn
1520-636Xjournal_volume
16pub_type
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