- Exo-functionalized shape-persistent [2+3] cage compounds: Influence of molecular rigidity on formation and permanent porosity
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Exo-functionalized [2+3] cage compounds were synthesized by using two different bissalicylaldehydes as molecular precursors in the reaction with triptycene triamine to study the influence of the rigidity of the molecular structure of [2+3] cages on their
- Schneider, Markus W.,Oppel, Iris M.,Mastalerz, Michael
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supporting information; experimental part
p. 4156 - 4160
(2012/06/01)
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- 18O-tracer studies of Fe(II)-induced decomposition of 1,2,4-trioxolanes (ozonides) derived from cyclopentenes and indenes. Inner-sphere electron transfer reduction of the peroxide linkage
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Fe(II)-induced decomposition of 1,2,4-trioxolanes (ozonides) 1 and 2 is studied in detail. The inner-sphere electron transfer reduction, which is sensitive to steric effects, is proposed to be a reasonable mechanism for the peroxide decomposition, i.e., the selective generation of one of the two possible Fe(III)-complexed oxy radicals. The fate of the oxy radical species is revealed in detail by using 18O-tracer studies in the reduction of 18O-labeled ozonides 1a and 2a, in which the ethereal oxygens are labeled by 18O atom (18O, 77%) and also by the reduction in the presence of H218O (18O, 10%). The results of the 18O-tracer studies are consistent with the regioselective generation of the Fe(III)-complexed oxy radical species.
- Abe, Manabu,Inakazu, Tomoyasu,Munakata, Johichi,Nojima, Masatomo
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p. 6556 - 6562
(2007/10/03)
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- Mechanistic Studies on the Photogenerated Dienol with α-Phenyl-N-tert-Butylnitrones
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The mechanism for the photochemical reactions of o-methyl-benzaldehyde (1), o-methyl-acetophenone (2) and o-methyl-benzophenone (3) in the presence of α-phenyl-N-tert-butylnitrone (PBN) to the formation of stable nitroxyl radicals 4-6 is studied. The nitroxyl radical product 6 can also be obtained by the thermolysis of benzocyclobutenol with PBN. Thus, the radical products were derived from a novel and regioselective 4+2 cycloaddition of the photogenerated dienol intermediate with PBN.
- Pan, Kai,Ho, Tong-Ing
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p. 243 - 247
(2007/10/03)
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- Selective Preparation of Polycyclic Aromatic Hydrocarbons. Part 7. A Preparative Route to 10,11-Dihydro-5H-dibenzo-cycloheptenes Using Friedel-Crafts Intramolecular Cyclobenzylation
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Cyclobenzylation of 2-hydroxymethyldiphenylethanes 4 and 2,2'-bis(hydroxymethyl)diphenylethanes 13 in the presence of a solid perfluorinated sulfonic acid resin, Nafion-H, as a catalyst results in novel polycyclic aromatic hydrocarbons, dibenzocyclopentenes.Dibenzocyclopentenes were also prepared from diphenylethanes by a benzylation reaction, which incorporates chloromethylation of a hydrocarbon followed by Friedel-Crafts intramolecular cyclization reaction.The present method involving the action of ClCH2OMe and TiCl4 on a variety of diphenylethanes (constructed such that electrophilic substitution occurs ortho to the diphenylethane linkage) offers a convenient, mild one-pot synthesis of substituted dibenzocycloheptenes.The mechanism of these reactions is also discussed.
- Yamato, Takehiko,Sakaue, Naozumi,Komine, Masayasu,Nagano, Yoshiaki
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p. 1708 - 1735
(2007/10/03)
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