Exploration into the (CH)4 hydrocarbon manifold - thermal stabilization pathway of rac-tritwistatriene

ZUSCHRIFTEN [C,H,Rh(=CPh,) (SbiPr,)][41 ist bisher nicht gelungen; der Angriff des sehr sperrigen Stibans auf die Rh-Rh-Doppelbindung wird vermutlich durch die vier Phenylgruppen der Carbenbrukken erheblich erschwert. Arbeilsvorschriften 4: Eine Losung von 98 mg (0.1 2 mmol) 1 in 10 mL Benzol wird unter Ruhren 4 h anf 60'C erwiirmt. Nach dem Ahkiihlen wird das Solvena entfernt, der Ruckstand (nach Waschen rnit Pentan) in 10 mL Ether geldst und dle Losung an AI,O, (neutral, Aktivititsstufe V, Saulenhohe 3 cm) chromatographiert. MIL Ether/Benzol (1 :2) wird eine rote Zone cluiert. ans der man nach Abziehen des Solvens imd Umkristallisation des Ruckstands aus Aceton (-78 'C) rote, an der Luft nur kurre Zeit stabile Kristalle isoliert; Ansbeute 42 ing (81 %,); Schmp. 190°C (Zers.). Die Synthese von 5 und 6 erfolgt analog: Ausbeute ca. 78 YO. 5: Schmp. 190 'C (Zers.); 6 : Schmp. 178°C (Zers.). 7: a) Eine Losung von XI mg (0.10 mmol) 1 in 10 mL Ether wird mit einer Losung von 22 mg (0.10 mmol) Di(p-to1yl)diazomethan in 5 mL Ether versctzt iind 3 h bei Raumtemperatur geruhrt. Das Solvens wird entfernt, der Ruckstand mehrmals mit Pentan gewdschen iind getrocknet; rotes mikrokristallines Pulver; Ausbeute 34 mg (76 %); Schmp. 183 "C (Zers.). b) Eine Losung von 47 mg (0.06 mmol) 4 und 49 mg (0.06 mniol) 5 in 10 mL Benzol wird 5 h hei Raumtemperatur geruhrt. Aufarbeitung wic unter a); Ausheute 93 mg (96 %).Angew'. C h m . 1994, 106, Nr. I Q VCH Vcrlugsgesellschufi mbH. 0-69451 Weinheim, 1994 0044-R249i94i0i01-OoRS $10.00+ ,2510 C v VClI Verlagsgesellsehaj~ mbH. 0-69451 R'uinheim, 1994 0044-8249/94/0i01-0086 S10.00i ,2510 Anget{,. Chem. 1994, 106, Nr. 1

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Isopagodane — Vorläufer ungewöhnlicher Käfig‐Ionen

Wollenweber

Pinkos

Leonhardt

et al. 1994

Angewandte Chemie

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Isopagodanes—Precursors of Unusual Cage Ions

Wollenweber

Pinkos

Leonhardt

et al. 1994

Angew. Chem. Int. Ed. Engl.

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COMMUNICATIONSence peak and hole: 310 enm-', R1 (F > 4a(F)) = 0.040 and wR2 = 0.095 (all data); R values as defined above. Data of both structures were collected on a Stoe-Siemens-AED diffractometer. The intensities of the rapidly cooled crystals in an oil drop [27] were collected by the 2 O/w method. Both structures were solved by direct methods (SHELXS-90) [28] and refined by full-matrix leastsquares on F1 [29].

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Functionalized Enantiomerically Pure [1.1.1]‐, [2.1.1]‐, [2.2.1]‐, and [2.2.2]Triblattanes

et al. 1993

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The methylene (2, 7, 10) and spirocyclopropane derivatives (8, 11, 12) are made accessible from rac-trishomocubane(mono-, di-, tri-)ones and optically pure unsaturated and benzoannulated [2.1.1]-(19, 48), [2.2.1]-(30, 53), and D3-symmetrical [2.2.2]triblattanes (3, 4) from the enantiomers of these ketones by expeditious (one pot) ring enlargement and olefination procedures. In the case of the central [2.2.2]trienes (+)-3/( -)-3, novel members of the (CH),, family, optical resolution is advantageously postponed to the stage of the intermediate [2.2.2]triones (35, 41) and effected via their (R,R)-2,3-butanediol acetals. In the a-diketone series only the [2.l.l]dione (70) is , and [2.2.2]Triblattanes 2277Demjanov procedure via 15/16r'71 or even 93% using the Schollkopf sequence via 13/14"'] was achieved. Scheme 2. i) N2HCC02Et/n-butyllithium/THF/-78 to -3 0 T / 97%.ii) C3H5Pd(I)C1 dimer/CH2Clz/-78 to room temp./96%. -iii) NaHC03/H20/150"C/1 h/100%.iv) TMSCN/Zn12/CH2C12. -v) LiAIHdTHF.vi) NaN02/H20/glacial acetic acid/iv-vi: 81 YO

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Exploration into the (CH)4 hydrocarbon manifold - thermal stabilization pathway of rac-tritwistatriene

Cited by 6 publications

References 18 publications

Isopagodane — Vorläufer ungewöhnlicher Käfig‐Ionen

Isopagodane — Vorläufer ungewöhnlicher Käfig‐Ionen

Isopagodanes—Precursors of Unusual Cage Ions

Functionalized Enantiomerically Pure [1.1.1]‐, [2.1.1]‐, [2.2.1]‐, and [2.2.2]Triblattanes

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