Two β,γ-disubstituted δ-valerolactones 2 and 3 were synthesized starting from (R)-(+)-limonene. The most significant conformations for each lactone were determined by molecular mechanics calculations; then the 1H-NMR coupling constants for each pair of vicinal hydrogen atoms of the lactone rings were calculated through suitable Karplus equations. Comparison of experimental and calculated coupling constants allowed the assignment of the vicinal stereorelationship between the β and the γ substituents in 2 and 3.
Cis and trans β,γ-disubstituted δ-valerolactones: conformational studies and configurational assignments by molecular mechanics / F. Ronchetti, L. Toma. - In: TETRAHEDRON. - ISSN 0040-4020. - 42:23(1986), pp. 6535-6540.
Cis and trans β,γ-disubstituted δ-valerolactones: conformational studies and configurational assignments by molecular mechanics
F. RonchettiPrimo
;
1986
Abstract
Two β,γ-disubstituted δ-valerolactones 2 and 3 were synthesized starting from (R)-(+)-limonene. The most significant conformations for each lactone were determined by molecular mechanics calculations; then the 1H-NMR coupling constants for each pair of vicinal hydrogen atoms of the lactone rings were calculated through suitable Karplus equations. Comparison of experimental and calculated coupling constants allowed the assignment of the vicinal stereorelationship between the β and the γ substituents in 2 and 3.
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