Spectroscopic, crystallographic and computational studies of the formation and isomerization of cyclic acetals and ketals of pentonolactones

So Yeop Han, Madeleine M. Joullié, Valery V. Fokin, Nicos A. Petasis

Research output: Contribution to journalArticle

25 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2535-2562
Number of pages28
JournalTetrahedron Asymmetry
Volume5
Issue number12
DOIs
Publication statusPublished - 1994
Externally publishedYes

Fingerprint

acetals
Acetals
Isomerization
Acetone
acetone
isomerization
reactivity
Molecular mechanics
Lactones
Mechanics
Nuclear magnetic resonance
X-Rays
Derivatives
X rays
nuclear magnetic resonance
products
x rays
ribonolactone
benzaldehyde
Carbon-13 Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Spectroscopic, crystallographic and computational studies of the formation and isomerization of cyclic acetals and ketals of pentonolactones. / Han, So Yeop; Joullié, Madeleine M.; Fokin, Valery V.; Petasis, Nicos A.

In: Tetrahedron Asymmetry, Vol. 5, No. 12, 1994, p. 2535-2562.

Research output: Contribution to journalArticle

Han, So Yeop ; Joullié, Madeleine M. ; Fokin, Valery V. ; Petasis, Nicos A. / Spectroscopic, crystallographic and computational studies of the formation and isomerization of cyclic acetals and ketals of pentonolactones. In: Tetrahedron Asymmetry. 1994 ; Vol. 5, No. 12. pp. 2535-2562.
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