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doi:10.1016/S0957-4166(00)80400-0 
Copyright © 1994 Published by Elsevier Science Ltd. All rights reserved.
Spectroscopic, crystallographic and computational studies of the formation and isomerization of cyclic acetals and ketals of pentonolactones*1
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So-Yeop Hanb, a, Madeleine M. Joullié, *a, Valery V. Fokinc and Nicos A. Petasis, *c
Received 14 October 1994.
Abstract
The different reactivities of D-ribonolactone, L-arabinonolactone, D-xylonolactone, D-lyxonolactone 2-deoxy-D-ribonolactone toward benzaldehyde and acetone in acidic media, were examined. The reactions involved complex equilibria and were investigated with extensive 13C NMR studies as well as X-ray crystallographic analysis of selected products. Molecular mechanics (MM2) and semiempirical (PM3 and AM1) calculations of some derivatives were carried out in order to facilitate structural and conformational assignments. The differences in reactivity observed for the reactions of D-pentono-1,4-lactones with benzaldehyde and acetone are rationalized in terms of their structural and conformational features.
Stereochemistry Abstract
C5H7O5 |
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C5H7O5 |
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5-O-Acetyl-2,3-O-(R)-benzylidene- C14H14O6 |
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3,5-(S)-Benzylidene- C12H12O5 |
|
3,5-O-(S)-Benzylidene- C12H12O5 |
|
3,5-O-Isopropylidene- C8H12O5 |
|
1,4:3,4-Di-O-isopropylidene- C11H18O6 |
|
2,3-O-Isopropylidene- C8H12O5 |
|
3,5-O-Isopropylidene- C8H12O5 |
|
Article Outline
*1 Presented in part at the 204th Meeting of the American Chemical Society Wanshigton, DC, August, 1992.
