Synthesis and rearrangement of dispiro[3.1.3.2]-, dispiro[3.0.3.3]- and dispiro[3.0.4.2]undecanes- new entries to [3.3.3]propellanes

Fitjer, Lutz; Kanschik, Andreas; Majewski, M.

doi:10.1016/s0040-4020(01)85699-4

Cited by 25 publications

(11 citation statements)

References 26 publications

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“…A comparison of the two Si(SiMe 2 Cl) 3 units shows that the silyl units containing Si (2) and Si(8) have a similar orientation, as is the case for Si (3) and Si (7) and Si(4) and Si (6). A look at the SiϪSiϪSi angles shows that all the SiϪSi(1)ϪSi(5) ands Si(1)ϪSi (5)ϪSi angles are larger than the tetrahedral angle of 109.5°, while all the SiϪSiϪSi angles within each Si(SiMe 2 Cl) 3 unit are smaller. This is a result of the mutual repulsion of the two Si(SiMe 2 Cl) 3 units connected by the central SiϪSi bond.…”

Section: Resultsmentioning

confidence: 83%

“…It should be mentioned that carbon-based [3.3.3]propellanes have been known for some time [4,5] and even a naturally occurring sesquiterpene, modhephene (3b), [6,7] containing this tricyclic skeleton has been described. Molecular structures have been reported for modhephenediol (3c, 2,3-dihydroxy-2,4,4,8-tetramethyl [3.3.3]propellane, [6] ) and [3.3.3]-propellane-2,8,9-trione (3d).…”

Section: Introductionmentioning

confidence: 99%

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3,7,10-Trichalcogenaoctasila[3.3.3]propellanes

Herzog

Rheinwald

2001

Eur. J. Inorg. Chem.

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The reaction of hexakis(trimethylsilyl)disilane with acetyl chloride and aluminum chloride yields hexakis(chlorodimethylsilyl)disilane (5a) under carefully controlled reaction conditions. Treatment of 5a with either H 2 S/NEt 3 or Li 2 E (E = Se, Te) gives the dodecamethyl-3,7,10-trichalcogenaoctasila-[3.3.3]propellanes Si 2 (SiMe 2 ) 6 E 3 (6a E = S, 6b E = Se, 6c E = Te). The products have been characterized by multinuclear NMR spectroscopy ( 1 H, 13 C, 29 Si, 77 Se, 125 Te). The central silicon atoms are very deshielded in comparison with other

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Section: Resultsmentioning

confidence: 83%

Section: Introductionmentioning

confidence: 99%

3,7,10-Trichalcogenaoctasila[3.3.3]propellanes

Herzog

Rheinwald

2001

Eur. J. Inorg. Chem.

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“…[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. MCRs have also been applied for the synthesis of propellanes.…”

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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“…7 Hexaaza [3.3.3]propellane, a heterocyclic propellane, is an example of an important energetic material used as a molecular explosive. 8 The commonest reported processes for the preparation of propellanes usually involve Diels-Alder reactions, 1,9 photochemical additions, 10 palladium 11 or manganese catalysis, 12 rearrangement of spiro-ketones, 13 and nucleophilic substitutions of 1,1,2,2-tetrasubstituted alkenes. 14 These processes are based on the introduction of a third ring on the framework of a fused bicyclic structure.…”

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confidence: 99%