Studies on hetero-cage compounds—VI

Sasaki, Tadashi; Eguchi, Shoji; Kiriyama, T.; Hiroaki, Osamu

doi:10.1016/s0040-4020(01)97433-2

Cited by 67 publications

(13 citation statements)

References 9 publications

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“…413±415 K). Compound (VI) was prepared by heating (III) with aniline in boiling benzene, in an analogous manner to a literature protocol (Sasaki et al, 1974), and was used for further reaction without puri®cation. The reactions of ketones (I) and (III), as well as aminoketone (VI), with trimethyl(tri¯uoromethyl)silane were performed in absolute 1,2-dimethoxyethane (DME) under an argon atmosphere in the presence of catalytic amounts (ca 10 mol%) of caesium¯uoride, which had been dried by preheating at 423 K for several hours (Roman Â ski & Mloston Â , 2005).…”

Section: Methodsmentioning

confidence: 99%

Trifluoromethyl derivatives of pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane

et al. 2005

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Three cage-like polycyclic compounds, viz. exo-8-(trifluoromethyl)pentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecan-endo-8-ol, C12H13F3O, 5-(trifluoromethyl)-4-oxahexacyclo[5.4.1.0(2,6).0(3,10).0(5,9).0(8,11)]dodecan-3-ol, C12H11F3O2, and N-[exo-11-(trifluoromethyl)-endo-11-(trimethylsilyloxy)pentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecan-8-ylidene]aniline methanol solvate, C21H24F3NOSi.CH4O, were obtained from the corresponding oxo derivatives by nucleophilic trifluoromethylation with (trifluoromethyl)trimethylsilane in 1,2-dimethoxyethane solution in the presence of CsF. The crystal structures show that the addition of trifluoromethanide occurs exclusively from the exo face of the polycyclic ketones. Further examination of the crystal structures, together with that of the starting pentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecane-8,11-dione, C11H10O2, showed that increasing substitution at the 8- and/or 11-positions in the cage molecules increases the non-bonded intramolecular C...C distances at the mouth of the cage and changes the puckering of the five-membered rings involving the 8- and 11-positions from an envelope towards a distorted half-chair conformation. Intermolecular co-operative O-H...O hydrogen bonds in the endo-8-ol compound link the molecules into tetramers.

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Section: Methodsmentioning

confidence: 99%

Trifluoromethyl derivatives of pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane

et al. 2005

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“…Pentacyclo[5.4.0.02'6.03'10.05 '9]undecane-8,ll-diol (6). A solution of 100 g of the dione obtained by irradiation of the p-benzoquinone-cyclopentadiene Diels-Alder adduct in 400 ml of anhydrous tetrahydrofuran was added under N2 to a mechanically stirred mixture of 30 g of L1AIH4 in 200 ml of anhydrous tetrahydrofuran.…”

Section: Methodsmentioning

confidence: 99%

Syntheses of the pentacyclo[6.3.0.02,6.03,10.05,9]undecyl (trishomocubyl) and tetracyclo[6.3.0.04,11.05,9]undeca-2,6-dienyl (homohypostrophenyl) systems

Smith¹,

Barborak²

1976

J. Org. Chem.

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“…, 39, 1596 chloride according to the procedure described by Sasaki and co-workers. 10 To a stirred suspension of dioxime 5 (2.04 g, 10 mmol) in dichloromethane (80 mL) was added a solution of 90% fuming HN03 (10 mL) in dichloromethane (80 mL) dropwise over a period of 15 min. During this period, the reaction became slightly exothermic, and the dioxime dissolved completely, resulting in a bluish green solution.…”

Section: Baeyer-villigermentioning

confidence: 99%