Cyclotriveratrylenes

FLUORINECOMPOUNDS,ORGANIC - POLY(FLUOROSILICONES)] (Volll) Cyclotriveratrylene [1180-60-5]... 

The work of Hyatt on cyclotriveratrylene—derived octopus molecules contrasts with this. Of course, these species have the advantage of ligand directionality absent in the benzene-derived octopus molecules. Except for the shortest-armed of the species (i.e., n = 1), all of the complexing agents (i.e., n = 2—4) were capable of complexing alkali metal cations. Synthesis of these species was accomplished as indicated below in Eq. (7.7). These variations of the original octopus molecules were also shown to catalyze the reaction between benzyl chloride and potassium acetate in acetonitrile solution and to effect the Wittig reaction between benzaldehyde and benzyltriphenylphos-phonium chloride. 

Raston has reported an acid-catalyzed Friedel-Crafts reaction [89] in which compounds such as 3,4-dimethoxyphenylmethanol were cyclized to cyclotriveratrylene (Scheme 5.1-57). The reactions were carried out in tributylhexylammonium bis(tri-fluoromethanesulfonyl)amide [NBu3(QHi3)][(CF3S02)2N] with phosphoric or p-toluenesulfonic acid catalysts. The product was isolated by dissolving the ionic liq-uid/catalyst in methanol and filtering off the cyclotriveratrylene product as white crystals. Evaporation of the methanol allowed the ionic liquid and catalyst to be regenerated. 

Collet, A., Dutasta, J.-P., Lozach, B., and Canceill, J. Cyclotriveratrylenes and Cryptophanes Their Synthesis and Applications to Host-Guest Chemistry and to the Design of New Materials. 165, 103-129 (1993). 

Cyclotriphosphazene hosts, 14 177-178 Cyclotrisiloxanes, 20 242 Cyclotriveratrylenes, 14 178 24 37 organometallic derivatives of, 24 44-45 Cycopac, composition, 3 386t Cylinder oil, 15 594 Cylinder paper former, 15 118—119 Cylinders, flows around, 11 753-757 15 720t... 

PPN = bis(triphenylphosphine)iminium TPP = tetraphenylporphyrinate IMes = 1,3-dimesitylimidazol-2-ylidene CTV = cyclotriveratrylene... 

The network structures to be discussed will all involved hydrogen bonding as the supramolecular synthon. It should be noted however that other interactions such as coordinate bonds and host-guest interactions may also organise host molecules into network structures. Coordination polymers constructed from molecular hosts may involve functionalised calixarenes [8-11], cyclotriveratrylene [12], or cucurbituril [13]. Calixarenes have also been used to build up network structures via host-guest interactions [14,15]. It is also notable that volatile species may be trapped within the solid state lattice of calix[4] arene with a structure entirely composed of van der Waals interactions [16]. 

In principle, there are four basic strategies to compensate for the repulsive effects between the hydrophobic fullerene surface and water (a) encapsulation in the internal hydrophobic moiety of water-soluble hosts like cyclodextrins (Andersson et al., 1992 Murthy and Geckeler, 2001), calixarenes (Kunsagi-Mate et al., 2004) or cyclotriveratrylenes (Rio and Nierengarten, 2002) (b) supramolecular or covalent incorporation of fullerenes or derivatives into water-soluble polymers (Giacalone and Martin, 2006) or biomolecules like proteins (Pellarini et al., 2001 Yang et al., 2007) (c) suspension with the aid of appropriate surfactants and (d) direct exohe-dral functionalization in order to introduce hydrophilic moieties. 

Rio Y, Nierengarten J-F (2002) Water soluble supramolecular cyclotriveratrylene-[60]fullerene complexes with potential for biological applications. Tetrahedron Lett. 43 4321 4324. 

In another example, a catalytic amount of a Bronsted acid such as H3PO4 was dissolved in [NRR 3][NTf2] (R = hexyl, R = butyl) 119). The catalyst was applied for the condensation reaction of alcohols, which usually requires strongly acidic media and dehydrating conditions. The condensation of veratryl alcohol was facilitated because the water that formed was continuously removed as vapor, which assisted in driving the reaction to high yields. The product (cyclotriveratrylene) separation, however, required the addition of a co-solvent. 

Typically, the cumulative electron-withdrawing effect of metallating more than half of the arenes of the macrocycle is required in order to observe anion inclusion. Thus, we have focused on tetrametallated derivatives of calix[4]arene and di- or trimetalated derivatives of the related orr/io-cyclophane, cyclotriveratrylene (CTV). The X-ray crystal structure of the BF salt of the water soluble bear trap 51 demonstrates the suitability of the narrow calix[4]arene cavity for small tetra-... 

Fig. la-e. Examples of frequently used building blocks for synthetic host molecules a calixarene b cyclotriveratrylene c resorcinol-aldehyde tetramer d Kemps triacid e Trogers base... 

Cyclotriveratrylenes and Cryptophanes Their Synthesis and Applications to Host-Guest Chemistry and to the Design of New Materials... 

The CH3-NH3+ cation forms a selective speleate 67 by binding to the [18]-N203 subunit of a macropolycycle maintained by a cyclotriveratrylene shaping cojnpo-nent. The tight intramolecular cavity efficiently excludes larger substrates [4.42, 4.54],... 

Fig. 15. Macrocyclic and oligocydic lattice hosts perhydrotriphenylene (32) a cyclotriphosphazene (33) cyclotriveratrylene (34) tri-o-thymotide (35).

Cyclotriveratrylene/1180-60-5] (34) is a cyclocondensation product of veratrole with formaldehyde. It possesses a stable trigonal crown conformation and forms crystalline inclusion compounds with benzene, chlorobenzene, toluene, thiophene, decalin, chloroform, acetone, carbon disulfide, acetic acid, and butyric acid (101). Their structures consist of columns of cyclotriveratrylene molecules that are not amenable to close packing and provide channels into which the guests are accommodated. A number of modified host structures, derived from prototype (34) have been prepared. The hexaphenol analogue cyclotricatechylene also yields well-defined channel inclusions (101). They involve mosdy polar guests and the structures are held by hydrogen bonding. 

Cyclotriveratrylene (CTV) Organic molecule Van der Waals/ crystal packing Clathrate (CTV) 0.5 (acetone)... 

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