Physical Image vs. Structure Relation. 9. Synthesis and Structural Study of Some 2,5-Bis-alkoxysubstituted 3-Oxolenes and Oxolanes: An Experimental and Theoretical Approach

• Autorzy: Nazarski R. , Skowroński R.
• Języki publikacji: EN

Abstrakty

EN

Two 2,5-bis-substituted 3-oxolenes 2 stable only in anhydrous, acid-free solutions were obtained in the Clauson-Kaas reaction. An immediate catalytic hydrogenation of theE/Z isomeric mixture of oxolene 2a, followed by chromatography, afforded one geometrical form of oxolane diol 4 (isomer I), which was subsequently submitted to several attempts of cyclization to an unknown bis-spiroacetal of succinic anhydride (6). Arationalization of this process failure and the Z geometry of product I exhibiting interesting spectroscopic features were inferred from theoretical results (HF/6-31G** calculations) and experimental data for solution (NMR, IR). Some additional ab initio GIAO-CPHF NMR computations concerning relevant model bis-acetals 3 and 5 were performed, as well.

Słowa kluczowe

EN

furan; diols; anhydride bis-acetals; stereochemistry; hydrogen bond; 12-member rings; molecular modelling; GIAO NMR calculations

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2003
• Tom: Vol. 77 / nr 4
• Strony: 415--426
• Opis fizyczny: Bibliogr. 34 poz., rys.

Twórcy

autor

Nazarski R.

• Department of Organic Chemistry, Institute of Chemistry, University of Łódź, P.O. Box 376, 90-950 Łódź 1, Poland

autor

Skowroński R.

• Department of Organic Chemistry, Institute of Chemistry, University of Łódź, P.O. Box 376, 90-950 Łódź 1, Poland

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