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- W2057302531 abstract "(3aRS, 9aSR, 9bSR)-Octahydro-1H-furo[3',4':4,5]isoxazolo[2,3-a]pyridin-1-one (C 9 H 13 NO 3 ), (4aRS,10aRS,10bRS)-octahydro-1H,3H-pyrano[3',4':4,5]isoxazolo-[2,3-a]pyridin-1-one (C 10 H 15 NO 3 ), and (5aRS,11aRs,11bRS)-decahydro-1H-oxepino[3',4':4,5]isoxazolo[2,3-a]pyridin-1-one (C 11 H 17 NO 3 ), exo products of the reaction between 3,4,5,6-tetrahydropyridine 1-oxide and five-, six- and seven-membered α,β-unsaturated lactones, adopt, in the solid state, the preponderant conformation observed in chloroform or acetone solution. The perhydroisoxazolo[2,3-a]pyridine substructure presents a cis fusion when the lactone ring is five-membered and a trans fusion when it is six- or seven-membered. In the three compounds, the piperidine ring exhibits a more or less distorted chair conformation depending on the product. The lactone ring conformation involves a local pseudo twofold axis running through the carbonyl C atom (five-membered lactone) or through the midpoint of the C-C bond that joins the carbonyl group to the ring junction (six- and seven-membered lactones). On the other hand, the isoxazolidine ring shows an envelope conformation when the lactone ring is six- or seven-membered, whereas an intermediate conformation between the envelope and the half-chair is observed when the lactone is five-membered." @default.
- W2057302531 created "2016-06-24" @default.
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- W2057302531 date "2010-08-17" @default.
- W2057302531 modified "2023-10-06" @default.
- W2057302531 title "ChemInform Abstract: Three Lactone Fused Perhydroisoxazolo(2,3-a)pyridines: A Conformational Study." @default.
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- W2057302531 doi "https://doi.org/10.1002/chin.199544030" @default.
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