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  • 1
    ISSN: 1573-1561
    Keywords: Antarctica ; marine benthos ; Tritoniella belli ; Mollusca ; nudibranch ; Clavularia frankliniana ; Cnidaria ; chemical defense ; predator ; prey ; chimyl alcohol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Extracts of the dorid nudibranchTritoniella belli and stoloniferan coralClavularia frankliniana were chromatographed and analyzed by1H NMR and thin-layer chromatography. Three glycerol ethers were detected inT. belli, primarily 1-O-hexadecyl glycerol (chimyl alcohol). Chimyl alcohol was also detected after gradient flash chromatography and reverse-phase HPLC purification in the tissues ofC. frankliniana. The common omnivorous predatory Antarctic sea starOdontaster validus, a likely predator of benthic invertebrates, showed feeding deterrence to small cubes ofT. belli mantle tissue placed on the tube feet along the ambulacral feeding groove, while always extruding the cardiac stomach when presented with cubes of shrimp tissue of similar size. Filter-paper disks soaked in an aqueous shrimp solution and then dried were found to elicit a broad range of feeding behaviors inO. validus, including movement of the shrimp disk to the mouth, extrusion of the cardiac stomach, and the assumption of a humped feeding posture. Chimyl alcohol-treated shrimp disks caused significant feeding deterrence in sea stars when compared with control disks (solvent plus shrimp treated disks alone).T. belli andC. frankliniana appear to employ a defensive compound that has been found in a variety of temperate and tropical mollusks, where it has been demonstrated to deter fish predators. We provide evidence for further deterrent capabilities of chimyl alcohol and of its trophic relationship in the polar ecosystem of McMurdo Sound, Antarctica.
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  • 2
    ISSN: 1573-1561
    Keywords: Antarctica ; sponge ; sea star ; Perknaster fuscus ; chemotactic ; repellent ; chemical defense ; polar ; marine benthos
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Hexane, chloroform, and methanol extracts of 18 species of antarctic sponges were tested for their ability to induce sustained tube-foot retraction in the antarctic spongivorous sea starPerknaster fuscus. Extracts were imbedded in silicone and used to coat the tip of a glass rod, which was allowed to contact an extended tube-foot. Retraction times were measured and compared with three controls: contact with a glass rod coated with a hexane extract of fish (feeding stimulant), contact with the glass rod alone (mechanical control), and contact with the glass rod coated with silicone alone (silicone control). Only extracts of the spongeMycale acerata did not elicit significantly longer tube-foot retraction times than controls for at least one of the three organic extracts. Hexane sponge extracts elicited the lowest levels of significant tube-foot responses, with only 39% of the sponge species tested showing activity in this fraction. In contrast, chloroform and methanol extracts elicited a significant tube-foot retraction response in 73% and 78% of the species tested, respectively. This indicates that in this assay repellent metabolites are generally more polar substances. It remains to be determined that secondary metabolites are responsible for all of the tube-foot retraction responses detected in sea stars exposed to sponge extracts; bioactive secondary metabolites have been isolated from a number of these antarctic sponges. It may be of ecological significance that the two rapidly growing sponges,Homaxinella balfourensis andMycale acerata, were either not repellent or had low repellency, and thatM. acerata is the primary dietary item ofPerknaster fuscus.
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  • 3
    ISSN: 0009-2940
    Keywords: Bulky substituents ; Aluminum compounds ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis and Structure of CpAlCl2 Compounds with Sterically Demanding Substituents (Cp = Me5C5, EtMe4C5)[1]The compounds Cp*AlCl2 (3) (Cp* = Me5C5) and Cp′AlCl2 (4) (Cp′ = EtMe4C5) have been prepared by the reaction of Cp*SiMe3 (1) and Cp′SiMe3 (2) with AlCl3. The single-crystal X-ray structures of 3 and 4 are reported.
    Additional Material: 2 Ill.
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  • 4
    ISSN: 0009-2940
    Keywords: Sulfur diimides ; 1,3-Cycloaddition, reductive ; 1,2,4,3-Thiadiazaboretidines ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis and Properties of 1,2,4,3-Thiadiazaboretidines. Crystal Structure of 2,4-Di-tert-butyl-3-phenyl-1,2,4,3-thiadiazaboretidineReaction of sulfur diimides with alkyl(aryl)bis(methylthio)boranes leads to reductive 1,3-cycloaddition of the NSN sequence with formation of the 1,2,4,3-thiadiazaboretidines 2a-g. NMR (1H, 11B, 13C, 15N, 29Si), mass spectra and the results of the X-ray analysis of 21 are reported and discussed. The 11B chemical shifts have been calculated for 3-phenyl-1,2,4,3-thiadiazaboretidine and some related model compounds by the IGLO method and correlate acceptably with the experimental values.
    Additional Material: 1 Ill.
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  • 5
    ISSN: 0009-2940
    Keywords: (Diisoalkylamino)boradiylbenzene derivatives ; Borolo[3,2-b]borole ; 2,8-Diborabicyclo[3.2.1]octa-3,6-diene ; Borylation of benzene derivatives ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Twofold Borylation of Benzene Derivatives with (Diisoalkylamino)boradiyl UnitsThe reaction of subvalent boron species generated by the defluorination of difluoro(diorganylamino)borane with Na/K alloy in the presence of 1,4-disubstituted benzene derivatives leads to products which contain two (diorganylamino)boradiyl units and two remaining double bonds which are located on the substituted C atoms. Compounds 5 to 8 exhibit structures based on a 2,8-diborabicyclo[3,2,1]octa-3,6-diene skeleton while 9 shows a skeleton with a 1,3a,4,6a-tetrahydroborolo[3,2-b]borole structure. The latter structure corresponds to that of 1 obtained in the same reaction with benzene. The compounds are characterized by elemental analyses and spectroscopically [MS, NMR (1H, 11B, 13C, 15N, 19F, 29Si)]. X-ray structure analyses are presented for 1, 6, 7, 8, and 9.
    Additional Material: 5 Ill.
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  • 6
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
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  • 7
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 293-294 
    ISSN: 0009-2940
    Keywords: 1,2,3-Triborolane / Dicyclopentadiene / Dichloro(diisopropylamino)borane, dehalogenation product of / Triborane(5), 1,2,3-tris(diisopropylamino)- ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (3α,4β,4aβ,7aβ,8β,8aα)-1,2,3-Tris(diisopropylamino)-1,2,3,3a,44a,5,7a,8,8a-decahydro-4,8-methanoindeno[5,6-d]-1,2,3-triborol (1) is formed from dicyclopentadiene and dichloro(diisopropylamino)borane upon treatment with sodium/potassium alloy in hexane. 1,2,3-Tris(diiso propylamino)triborane(5) (2) was also obtained. 1 is characterized by elemental analyses, spectroscopic data, and by an X-ray structure analysis, 2 by its MS and NMR data.
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  • 8
    ISSN: 0009-2940
    Keywords: 1,3,5,7-Cyclooctatetraene / 9-Borabicyclo[4.2.1]nona-2,4,7-triene, 9-(diisopropylamino)- / Borane, dihalogeno(diisopropylamino)- ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction of 1,3,5,7-cyclooctatetraene with sodium-postassium alloy and dihalogeno(diisopropylamino)boranes in 1,2-dimethoxyethane gives the title compound, characterized by elemental analysis, MS (EI, FI), NMR (1H, 11B, 13C), and X-ray crystallography.
    Additional Material: 1 Ill.
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  • 9
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Zeitschrift für anorganische Chemie 608 (1992), S. 147-152 
    ISSN: 0044-2313
    Keywords: 2,4,6-Tri-t-butylphenyl-substituted amino-imino boranes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Supermesityl stabilized IminoboranesAmino-iminoboranes R′(SiMe3)N-B≡N-R: IIc (R′ = CHMe2), IId (R′= CMe3) and IIe (R′ = SiMe3) carrying the supermesityl group (R) on the imino nitrogen atoms have been prepared from the corresponding fluorobis(amino)boranes Ic-e by HF-elimination using t-BuLi (IIc, d) or n-lithio-bis(trimethylsilyl)amid (IIe). The Amino-iminoboranes are thermally stable at room temperature. Upon treatment of the fluorobis(amino)boranes Ia, Ib, Ie with t-BuLi, LiF and HN(SiMe3)R′ are eliminated and the B-t-butyl substituted iminoborane III is formed. The compounds are characterized by elementar analyses and spectroscopic data (MS, IR, NMR). An X-ray diffraction study has been performed for II d.
    Notes: Amino-imino-borane R′(SiMe3)N-B≡N-R:IIc (R′ = CHMe2), IId (R′= CMe3) und IIe (R′ = SiMe3) mit R = 2,4,6-Tri-t-butylphenyl- wurden aus den entsprechenden Fluorbis(amino)boranen Ic-e durch HF-Eliminierung mit t-Butyllithium (IIc, IId) bzw. Lithiumbis(trimethylislyl)amid (IIe) erhalten. IIc-e sind thermisch stabil und bei Raumtemperatur unbegrenzt haltbar. Die Umsetzungen der Fluorbis(amino)borane Ia (R′ = Me), Ib(R′ = CH2Me) und Ie (R′ = SiMe3) mit t- Butyllithium führen zur Abspaltung von LiF und HN(SiMe3)R′, wobei sich in allen Fällen des B-t-butyl-substituierte Iminoboran III bildet. Die Verbindungen sind elementaranalytisch und spektroskopisch (MS, IR, NMR) charakterisiert. Eine Röntgenstrukturanalyse wurde von IId durchgeführt.
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