Tolane

Figure 2-53. Tolane rotamers a) one with the two aromatic rings in the same plane, and b) one with the two rings perpendicular to each other.

Cobalt, cyclopentadienyl(ij -tolane)-(triphenylphosphine)-reaction with phenyl isocyanide, 1, 666 Cobaltacycles selenophenes from, 4, 968 Cobaltacyclopentadienes reactions, I, 671 Cobester... 

P. Miiller-Buschbaum, M. Tolan, W. Press, F. Brinkop, J. P. Kotthaus. Wetting of laterally structured surfaces. Ber Bunsenges Phys Chem 95 413—414, 1994. 

Using a suspension of silver salts in alcohol or acetonitrile for isomerization of tolane-2-carboxylic acid leads to a change in the ratio between the resulting... 

An unusual cyclization, which results in carbocycles rather than heterocycles, was described in (69JCS2453). The reaction between o-iodobenzamides and copper phenylacetylides in pyridine leads to indanone (74%) rather than tolane (Scheme 124). 

Bond-Huper [69JCS(C)2453] synthesis, no traces of the described high-melting dark red substance were found. Only tolane-2-carboxylic acid amide (yield 65%) was obtained—the white crystals with a melting temperature of 156-157°C— which coincided with the results of Castro et al. (66JOC4071). Thus, in conditions of acetylide synthesis, o-iodobenzamide forms no bicyclic product. 

The German ending -an should be translated -ane if it is the name of a hydrocarbon (or parent heterocyclic compound) which is fully saturated otherwise, -an. Examples methane, menthane, tolan, furan, pentosan. 

Aus Fluor-halogen-olefinen werden dagegen wegen der mit Fluor leicht ablaufenden nucleophilen Substitutionsreaktionen Substitutionsprodukte (z. B. Tolan mit Phenyl-lithium aus Trifluor-brom-athylen oder l,2-Difluor-l,2-dichlor-athylen) erhalten (s. ds. Handb., Bd. V/2a, S. 42ff.). 

Die Reduktion von cis- und frarcs-a,/3-Diacetoxy-stilben in DMF/Tetrabutylammo-niumjodid an Quecksilber (-1,5 V vs. Ag/AgJ) fiihrt zu Tolan und bei —1,8 Volt zu trans-Stilben2. 2-Oxo-4-methyl-l,3-dioxolan wird an Graphit mit Lithiumperchlorat als Leitsalz unter C-O-Spaltung zu Propen reduziert3 ... 

Wahrend bei der Elektrolyse von Tolan fast ausschlielJlich 1,2-Diphenyl-athan entsteht (s. S. 577), erhalt man in Gegenwart von Kohlendioxid neben meso-2,3-Diphenyl-bern-steinsdure (27% d.Th.) und wenig 2,3-Diphenyl-bernsteinsaure-anhydrid 9° , d.Th. Di-phenyl-maleinsaure3. 

Small chemical changes to the tolane family of mesogenic molecules are also known to bring about major changes in phase behaviour [22]. Two examples are shown in Fig. 5 where subtle changes in the tail can eliminate the nematic phase. 

Fig. 5a,b. Tolane compounda a melts at 39 °C and is not mesogenic . b differs only in one tail substituent melts to a nematic phase at 61 °C which persists until 89 °C... 

Zareba et al. [165] described the crystal structure of the chiral 4-(l-methyl-heptyloxycarbonyl)-phenyl 4-heptyloxytolane-4 -carboxylate (C7-tolane) which shows monotropic antiferroelectric and ferroelectric phases. The single-crystal X-ray analysis of this compound shows that the crystal has a smectic-like layer structure composed of largely bent molecules where the chain of the chiral group is almost perpendicular (86°) to the core moiety. Within the layers, the molecules are tilted. The central tolane group of the molecule is roughly planar. 

The intramolecular approach of Staab and Graf, shown in Scheme 4, precluded formation of 5, but was considerably more involved [12]. The cyclic dienyne 6 was afforded by Wittig reaction of o-phthaldialdehyde with the corresponding bis(ylide) derived from tolane. Bromination of 6 and subsequent treat-... 

Irvine JD, Takahashi L, Lockhart K, Cheong J, Tolan JW, Selick HE, et al. MDCK (Madin-Darby canine kidney) cells a tool for membrane permeability screening. J Pharm Sci 1999 88 28-33. 

Irvine, J. D., Takahashi, L., Lockhart, K., Cheong, J., Tolan, J. W., Selick, H. E., Grove, J. R. MDGK (Madin-Darby canine kidney) cells a tool for... 

R6. Rottmann, W. H., Tolan, D. R., and Penhoet, E. E., Complete amino acid sequence for human aldolase B derived from cDNA and genomic clones. Proc. Natl. Acad. Sci. U.S.A. 81, 2738-2742 (1984). 

T16. Tolan, D. R Molecular basis of hereditary fructose intolerance Mutations and polymorphisms in the human aldolase B gene. Hum. Mutat. 6,210-218 (1995). 

A Cu-catalyzed domino reaction has been developed by Cacchi and his group [305] for the synthesis of pyrrolo[2,3-b]quinoxalines 6/4-101 using a 2-bromo-3-tri-fluoroacetamido quinoxaline 6/4-98 and a tolane 6/4-99 containing electron-donating or -withdrawing groups as substrates, and with 6/4-100 as a proposed intermediate (Scheme 6/4.24). 

The sigmatropic rearrangement of 1//-phospholes to the 2H derivatives gives a new entry to novel 1-phosphanorbomadienes after trapping with tolane. 

Tolan, A. (1974). Studies on the composition of food the chemical composition of eggs produced under battery, deep litter and free-range conditions , British Journal of Nutrition, 31, 185-189. 

This type of solid was synthesized with complexes such as [HRh(CO) PPh2(CH2)3S= 3] and [ClRuH P(0)(CH2)3Si= 3] (which were tested as catalysts for the hydrogenation and hydroformylation of tolan), and [(dba)Pd P(0)(CH2)3Si= 2] (tested for copolymerization reactions). 8-91 The activity and the selectivity of these catalysts are in all cases solvent-dependent, a phenomenon explained by their swelling ability. The authors claim that no leaching is occurring. 

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