In an article, published in an article, once mentioned the application of 1806-29-7, Name is 2,2-Biphenol,molecular formula is C12H10O2, is a conventional compound. this article was the specific content is as follows.Computed Properties of C12H10O2
The influence of substituents in close proximity to crown ether cavities, on the stability of complexes of the crown ethers with t-butylammonium salts, has been investigated.Crown ethers with intra-annular donor substituents (2-4) were prepared by the reaction of 2-acetylresorcinol (1) with polyethylene glycol ditosylates and subsequent modification of the acetyl group.Crown ethers with substituents above and below the plane of the crown ether O atoms were synthesized by the reaction of 2,2′-dihydroxy-1,1′-biphenyls with polyethylene gycol ditosylates.Chloromethylation of 5,5′-dimethyl-1,1′-biphenyl crown ethers (6) yielded 4,4′-bis(chloromethyl)-1,1’biphenyl crown ethers (10). 3,3′-Disubstituted-1,1′-biphenyl crown ethers (13-24) were synthesized by the reaction of 3,3′-diallyl-2,2′-dihydroxy-1,1′-biphenyl (12) with polyethylene glycol ditosylates.The allyl groups of 13 were isomerized with sodium hydride to propen-1-yl groups.Ozonolysis of 13 and 14 gave the corresponding dialdehydes (15 and 18) which were converted into other 3,3′-disubstituted biphenyl-20-crown-6 derivatives (R=CH2COOMe, CH2COOH, CH2OH, CH2Cl, CH2OMe, OH and Me) by standard operations.The thermodynamic stability of the complexes of these functionalized crown ethers with t-butylammonium hexafluorophosphate has been studied in deuterochloroform in competition experiments with m-xyleno-18-crown-5 and benzo-15-crown-5 as the reference compounds.The nature of the 2-substituents in the crown ethers 2 and 3 has little effect on the stability of the complexes.The stability of the complexes of 3,3′-disubstituted biphenyl crown ethers depends of ringsize and the size and nature of the substituents.The most stable complexes are those of 24 (R = Me) and 14 (R=CH=CHMe).The Me groups in 24 represent the optimum between relief of O-O repulsion in the polyether ring and steric hindrance of complexation.The propen-1-yl substituents of 14 stabilize the complex because they provide extended ?-electron donor stabilization.Substitution at the 4- and 4′-positions of the aryl groups has little effect on the stability of the complexes.
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