Über Verbindungen mit Urotropin‐Struktur, XLI. Ringschlußreaktionen ausgehend von Cyclooctadien‐(1.5)

Stetter, Hermann; Meißner, H.; Last, Wolf‐Dieter

doi:10.1002/cber.19681010838

Cited by 28 publications

(6 citation statements)

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“…Such a transannular S ‐heterocyclization was reported almost simultaneously by Stetter et al59 and by Ganter and Wicker more than three decades ago 62. According to the published procedure,59 treatment of the diene (±)‐ 9 with dichlorosulfane gave, after chromatographic purification, 4,8‐dichloro‐2‐oxa‐6‐thiaadamantane [(±)‐ 10 ] as a single diastereomer in 45% yield via the episulfonium ion I (Scheme ).…”

Section: Resultsmentioning

confidence: 91%

“…However, such an arrangement is possible in a boat conformation. Thus, treatment of (±)‐ 8 with KOH in ethanol at 120 °C in an autoclave for 96 hours59 gave 40% of the diene (±)‐ 9 . By modification of a protocol of Stetter and Heckel,60,61 we obtained the diene (±)‐ 9 as a crystalline compound in 88% yield by refluxing the diiodide (±)‐ 8 with dicyclohexylmethylamine.…”

Section: Resultsmentioning

confidence: 99%

“…4,8‐Dichloro‐2‐oxa‐6‐thiatricyclo[3.3.1.1 3,7 ]decane [(±)‐10]: Synthesized according to a known procedure59 from 9‐oxabicyclo[3.3.1]nona‐2,6‐diene [(±)‐ 9 ] (12.5 g, 0.102 mol) and SCl 2 (10.5 g, 0.102 mol) in dry CH 2 Cl 2 (250 mL). Purified by column chromatography (cyclohexane/ethyl acetate, 1:1).…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of Enantiopure 9‐Oxabicyclononanediol Derivatives by Lipase‐Catalyzed Transformations and Determination of Their Absolute Configuration

2004

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Keywords: Alcohols / Chiral resolution / Diols / Enantioselectivity / Lipases / Polycycles Mixtures of endo,nonane-2,6-diol [(±)-3] were prepared from cycloocta-1,5-diene (1) upon treatment with peracids by transannular O-heterocyclization and subsequent saponification of the formed diol monoesters such as (±)-4 and (±)-5. The corresponding diacetates, meso-6 and (±)-7, were formed by acetylation of either meso-2 and (±)-3 or (±)-4 and (±)-5 with acetic anhydride/pyridine. These diacetates were enantioselectively hydrolyzed by microbial enzymes such as the lipases from Candida antarctica (CAL) or Candida rugosa (CRL). The corresponding enantiomers were formed by lipase-catalyzed acetylation of the diols meso-2 and (±)-3 with vinyl acetate. The skeletal isomers can also be separated in this way because the enantiopure monoacetates 4 were formed from the meso-compounds 2 or 6, while one enantiomer of the racemic diacetate (±)-7 [or the diol (±)-3] was transformed into the enantiopure diol 3 (or the enantiopure diacetate 7, respectively) via the corresponding

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Section: Resultsmentioning

confidence: 91%

Section: Resultsmentioning

confidence: 99%

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Synthesis of Enantiopure 9‐Oxabicyclononanediol Derivatives by Lipase‐Catalyzed Transformations and Determination of Their Absolute Configuration

2004

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“…: 2775W, 16758, 14333, 1401", 1351m, 132lm. 1284m, 1264w, 1267w, l l l l w , 1052~0, 1043m, 998m, 9821u, 953m, 921~0, 862~0, 8 4 8~, 648 Gef. C 42,78 H 4,40 ru ' 5,. 100 mg (0,397 mMol) 13 und 1 g (6,67 mMol) X a J in 15 in1 Diathylketon wurden 2 Tage unter Hiickfluss gekocht (N,).…”

Section: ~~-unclassified

“…100 mg (0,397 mMol) 13 und 1 g (6,67 mMol) X a J in 15 in1 Diathylketon wurden 2 Tage unter Hiickfluss gekocht (N,). Das Gcmisch wurde abgedampft, der Riickstand mit 5 . I R .…”

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Synthese von 2‐Thia‐6‐aza‐adamantan und Derivaten

Ganter¹,

Portmann²

1971

Helvetica Chimica Acta

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Summary. The synthesis of 2-thia-6-aza-adamantane (19) and several of its derivatives was achieved starting from 9-azabicyclo[3.3.l]nona-2,6-diene (9) which was prepared from cis, ciscycloocta-l,5-diene (1). Transannular addition of sulfur dichloride to its N-benzenesulfonyl and N-formyl derivatives 10 and 11 yielded the tricyclic dichlorides 12 and 13, respectively; the 2-thia-6-aza-adamantanes 14-19 were synthesized from 13.In der vorliegenden Mitteilung berichten wir iiber einen einfachen Zugang zu Verbindungen vom Typus des bisher unbekannten 2-Thia-6-aza-adamantans (vgl. 12-19) 2 ) , ausgehend von cis, cis-Cyclooctadien-(l,5) (1). Fur die Darstellung der tricyclischen 2-Thia-6-aza-adarnantane verwendete man das 9-Azabicyclo[3.3.l]nonadien-(2,6) (9) in Form seiner N-Benzolsulfonyl-und uber einen Teil der Resultate wurde bereits an der Friihjahrsversammlung der Schweiz. Chem. Ges.

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Über Verbindungen mit Urotropin‐Struktur, LII. Ringschlußreaktionen auf der Basis von cis,cis‐1,5‐Cyclo‐octadien

Stetter

Heckel

1973

Chem. Ber.

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Ausgehend von cis,cis-I ,5-Cyclooctadien (1) werden neue Methoden zur Darstellung von 9-0xabicyclo[3.3. I]nona-2,6-dim (15) und N-(p-Toluolsulfonyl)-9-azabicyclo[3,3,1]nona-2,6dicn (6) bcschrieben. Die Schwefeldichloridanlagerung an 6 oder dessen Hydroxybromierung fiihrcn Z u n i 2-Thia-6-azaadamantan-System 20 und zum 2-Oxa-6-azaadamantan-System 21. I h r c h die Reaktion von N,N-Dibrom-p-toluolsulfonamid (11) mit bicyclischen Diolefinen (12, 6,15) wird ein einfacher Zugang ZLI Verbindungen vom Typ des 2-Azaadamantans (14a), 2,(,..I)iazaadaniantans (19a) und 2-Oxa-6-azaadamantans (17a) eroffnet. Compounds with Urotropin Structure, LII I) Cyclization Reactions with cis,cis-1,5-Cyclooctadiene as the Precursor ' )New methods for the preparation of 9-oxabicyclo[3.3.ljnona-2,6-diene (15) and N-(p-tolu-cncs~1lfonyI)-9-azabicyclo[3.3.1]nona-2,6-diene (6) are described using cis,cis-l,5-cyclooctadiem (1) as the precursor. The addition of sulfurdichloride to 6 or the hydroxybromination of 6 leads to the 2-thia-6-azaadamantane system 20 and to the 2-oxa-6-azaadamantane system 21. The rcaction of N,N-dibromo-p-toluenesulfonaniide (11) with bicyclic diolefines (12, 6,15) gives an easy access to compounds such as 2-azaadamantane (14a), 2,6-diazaadamantane (19a) and 2-oxa-6-azaadamantane (17a).

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Über Verbindungen mit Urotropin‐Struktur, XLI. Ringschlußreaktionen ausgehend von Cyclooctadien‐(1.5)

Cited by 28 publications

References 8 publications

Synthesis of Enantiopure 9‐Oxabicyclononanediol Derivatives by Lipase‐Catalyzed Transformations and Determination of Their Absolute Configuration

Synthesis of Enantiopure 9‐Oxabicyclononanediol Derivatives by Lipase‐Catalyzed Transformations and Determination of Their Absolute Configuration

Synthese von 2‐Thia‐6‐aza‐adamantan und Derivaten

Über Verbindungen mit Urotropin‐Struktur, LII. Ringschlußreaktionen auf der Basis von cis,cis‐1,5‐Cyclo‐octadien

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