Spirane—VIII

Smoliński, S.; Deja, L.

doi:10.1016/s0040-4020(01)98006-8

Cited by 10 publications

(2 citation statements)

References 3 publications

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“…A previous synthesis of SBINOX ( 5 ) was reported in 1971 by Smoliński and Deja, who obtained the compound in 8% yield by heating pentaerythrityl tetrabromide with the sodium salt of ( ± )-BINOL, followed by crystallization of the crude product. Analysis of stereomodels suggested to Smoliński and Deja that they had obtained a racemic mixture of the ( S , S ) and ( R , R ) enantiomers of SBINOX ( 5 ) rather than the meso ( R , S ) isomer, but the product was characterized only by IR spectroscopy, UV spectroscopy, and elemental analysis.…”

Section: Resultsmentioning

confidence: 94%

“…Crude SBINOX ( 5 ), obtained as a statistical mixture of the ( S , S ), ( R , S ), and ( R , R ) isomers from the reaction of (±)-BINOL with pentaerythrityl tetratosylate, was crystallized by exposing a solution in CH 2 Cl 2 to vapors of hexane. Contrary to the conclusions of Smoliński and Deja, the resulting crystals proved to consist solely of the meso ( R , S ) isomer, and the ( S , S ) and ( R , R ) isomers were absent. The crystals were found to belong to the orthorhombic space group P 2 1 2 1 2 1 .…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Structure of Spirocyclic Tetraethers Derived from [1,1′-Binaphthalene]-2,2′-diol and Pentaerythritol

Maris

Wuest

2008

J. Org. Chem.

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Molecular scaffolds that have well-defined geometries, are easy to synthesize and functionalize, and can hold attached sites of molecular recognition in suitable orientations are useful tools in various areas of science and technology. The utility of the tetraphenyl ether of pentaerythritol (4) as a scaffold in crystal engineering led us to study rigidified analogue SBINOX (5), the spirocyclic tetraether derived from pentaerythritol and [1,1'-binaphthalene]-2,2'-diol (BINOL). We have found that SBINOX (5) and derivatives can be prepared conveniently in acceptable yields and in stereoisomerically pure (S,S), (R,S), and (R,R) forms. X-ray crystallographic studies have revealed that the benzannulated 9-membered dioxonane rings in these structures adopt characteristic conformations of C1 symmetry. Intraannular C-H...O interactions help maintain the conformations of the individual rings, and the geometry of the spirocyclic SBINOX core is also controlled in part by distinctive short interannular C-H...O and C-H...pi interactions. Despite the inherent flexibility of the dioxonane rings, derivatives of SBINOX (5) can be expected to orient peripheral substituents in preferred ways, making SBINOX a potentially useful scaffold for applications in drug discovery, crystal engineering, and other fields.

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Section: Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 99%

Synthesis and Structure of Spirocyclic Tetraethers Derived from [1,1′-Binaphthalene]-2,2′-diol and Pentaerythritol

Maris

Wuest

2008

J. Org. Chem.

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ChemInform Abstract: SPIRANE 8. MITT. 3,3′‐SPIROBIS(DINAPHTHO(1,2‐F, 1′,2′‐H)‐(1,5)‐DIOXACYCLONONAN), KONFORMATIONALE TRANSMISSION IN SPIRANEN

Smoliński¹,

Deja²

1971

Chemischer Informationsdienst. Organische Chemie

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Synthese von 2,7,12,17‐Tetraoxa‐teranaphtho‐(1,2‐f h f′h′)‐dispiro[8.0.8.1]‐nonadecan‐ein Vertreter des[8.0.8.1] Dispiran‐Typs

Jamrozik¹

1985

J. Prakt. Chem.

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Synthesis of 2,7,12,17‐Tetraoxa‐tetranaphtho‐(1,2‐fhf′h′)‐dispiro[8.0.8.1]‐nonadecanes‐An Example of [8.0.8.1] Dispiranes In einer früheren Mitteilung[1] wurden Dispiran‐Systeme beschrieben, welche Repräsentanten der Klasse [6.0.6.1] waren. Die Synthesen dieser Dispirane erfolgten durch Kondensation des 1,1,2,2‐Tetrakis(brommethyl)cyclopropans mit 1,2‐Diolen,in die gegenseitige Lage der funktionellen Gruppen jedesmal fixiert und genau bestimmt war. Gegenstand der vorliegenden betrachtungen sind Versuche, eine Synthese des [8.0.8.1]‐Dispirans auf ähnlichem Wege, wenn auch unter Verwendung labiler Diphenole auszuarbeiten. Zu diesem Zweck wurden zwei reaktive Diphenole mit extrem verschiedenen Rotationsmöglichketen um die Einfachbindung gewählt.

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Spirane—VIII

Cited by 10 publications

References 3 publications

Synthesis and Structure of Spirocyclic Tetraethers Derived from [1,1′-Binaphthalene]-2,2′-diol and Pentaerythritol

Synthesis and Structure of Spirocyclic Tetraethers Derived from [1,1′-Binaphthalene]-2,2′-diol and Pentaerythritol

ChemInform Abstract: SPIRANE 8. MITT. 3,3′‐SPIROBIS(DINAPHTHO(1,2‐F, 1′,2′‐H)‐(1,5)‐DIOXACYCLONONAN), KONFORMATIONALE TRANSMISSION IN SPIRANEN

Synthese von 2,7,12,17‐Tetraoxa‐teranaphtho‐(1,2‐f h f′h′)‐dispiro[8.0.8.1]‐nonadecan‐ein Vertreter des[8.0.8.1] Dispiran‐Typs

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