Propellane, 11. Mitt.: Synthese von Dioxa[4.3.3]propellanen aus vicinalen Tetrakis(hydroxymethyl)cycloalkanen

Jamrozik, J.; Jamrozik, M.; Ściborowicz, P.; Zeslawski, W.

doi:10.1007/bf00807433

Cited by 11 publications

(2 citation statements)

References 9 publications

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“…Compounds 2 and 3 were obtained in 21 and 34% overall yields from anhydrides 5 and 4 , respectively, by following a literature strategy of the construction of a tetrahydrofuran ring . The syntheses included acidic methanolysis of anhydrides 5 and 4 followed by reduction of diester 6 and tetraester 8 to diol 7 and tetraol 9 and, finally, dehydration of the latter with KHSO 4 .…”

Section: Resultsmentioning

confidence: 99%

exo,exo-4,8-Ethenopolyfluoro-2,6-dioxaperhydroindacenes. Unusual Alkenes Flanked with Fluorine Atoms

Dmowski¹,

Nowak²,

Gluziński³

et al. 1997

J. Org. Chem.

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6-dioxaperhydroindacene (2), as well as their nonfluorinated analogue 3 were synthesized. The structures of 1 and 3 have been determined in the solid state by X-ray crystallography and of all three compounds in solution by 1 H, 19 F, and 13 C NMR spectroscopy. The chemical properties of compounds 1-3 were investigated and compared. The double bond in fluorinated polycycloalkenes 1 and 2 was found to be totally inert toward bromination, hydrogenenation, and oxidation with m-chloroperbenzoic acid and ozone. This is in contrast to nonfluorinated indacene 3, which behaves like a normal alkene, readily adds bromine and hydrogen, and reacts with oxidants. The only successful chemical transformation of 1 was achieved by treatment with Mn 2 O 7 , which led to oxirane 15 and rearranged pentacyclic acetal 16. An interesting skeletal rearrangement occurred in the course of bromination of 3 leading to bicyclic tetrabromo derivative 12. High chemical inertness of polyfluoroindacenes 1 and 2 has been attributed mainly to through-space electronic interactions of the double bond with proximal fluorine atoms.

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Section: Resultsmentioning

confidence: 99%

exo,exo-4,8-Ethenopolyfluoro-2,6-dioxaperhydroindacenes. Unusual Alkenes Flanked with Fluorine Atoms

Dmowski¹,

Nowak²,

Gluziński³

et al. 1997

J. Org. Chem.

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“…[11] Although, much later, in 1965, the first 'propellane was designed and constructed. [12,13] Various methods have been reported for the synthesis of propellanes including Diels-Alder reaction, [14] photochemical additions, [15] manganese [16] or palladium [17] catalysis, nucleophilic substitutions of 1,1,2,2-tetrasubstituted alkenes [18] and rearrangement of spiro-ketones. [19] These processes are based on the introduction of a third ring on the framework of a fused bicyclic structure.…”

Section: Introductionmentioning

confidence: 99%

Chemo‐ and diastereoselective synthesis of new oxa[3.3.3]propellane via a domino cascade four‐component reaction based on diketene

Rezvanian

Salimi

Zadsirjan

et al. 2020

Journal of Heterocyclic Chem

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A highly convergent, eco-friendly and straightforward synthesis of new O-fused heterocycles, functionalized indeno[1,2-b]furan derivatives was successfully accomplished through a one-pot four-component cascade reaction involving, ninhydrin, malononitrile, diketene and various primary amines in the presence of a catalytic quantity of triethylamine in ethanol at ambient temperature, in one pot fashion. This new efficient cascade reaction generates two rings by the simultaneous construction of C-N (one), CO (two) and CC (two) multiple bonds, presumably through a sequence of Knoevenagel reaction/ Michael addition/intramolecular O-cyclization and imine-enamine/keto-enol tautomerization. The merits of this protocol are highlighted as utilization of inexpensive commercially accessible starting materials, operational simplicity, atom economy, clean reaction profile, simple work-up procedure being conducted at ambient temperature in relatively short reaction times, preventing chromatographic purification, giving excellent yields, and tolerance to a wide variety of functional groups.

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ChemInform Abstract: Propellanes. Part 11. Synthesis of Dioxa(4.3.3)propellanes from Vicinal Tetrakis(hydroxymethyl)cycloalkanes

Jamrozik¹,

Jamrozik²,

Ściborowicz³

et al. 1995

ChemInform

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Propellane, 11. Mitt.: Synthese von Dioxa[4.3.3]propellanen aus vicinalen Tetrakis(hydroxymethyl)cycloalkanen

Cited by 11 publications

References 9 publications

exo,exo-4,8-Ethenopolyfluoro-2,6-dioxaperhydroindacenes. Unusual Alkenes Flanked with Fluorine Atoms

exo,exo-4,8-Ethenopolyfluoro-2,6-dioxaperhydroindacenes. Unusual Alkenes Flanked with Fluorine Atoms

Chemo‐ and diastereoselective synthesis of new oxa[3.3.3]propellane via a domino cascade four‐component reaction based on diketene

ChemInform Abstract: Propellanes. Part 11. Synthesis of Dioxa(4.3.3)propellanes from Vicinal Tetrakis(hydroxymethyl)cycloalkanes

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