- Synthesis of [n]- and [n.n]Cyclophanes by using Suzuki-Miyaura coupling
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Reaction of the bis-9-BBN adduct of several dienes with 1,3-dibromobenzene via Suzuki coupling leads to a series of [n]metacyclophanes ranging in size from 10 to 17 atom members. In each case, two carbon-carbon bonds are formed in one reaction vessel. However, when the bis-9-BBN adduct of 1,5-hexadiene is coupled with a variety of aryl dihalides, larger [n.n]cyclophanes were formed in preference to the [n]cyclophanes. Four carbon-carbon bonds are formed in this instance. Single-crystal X-ray analyses of these [n.n]cyclophanes reveal interestingly shaped molecules with large cavities.
- Smith, Beverly B.,Hill, Darron E.,Cropp, T. Ashton,Walsh, Rosa D.,Cartrette, David,Hipps, Sherry,Shachter, Amy M.,Pennington, William T.,Kwochka, William R.
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p. 5333 - 5337
(2007/10/03)
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- Synthesis and Dynamic Behaviour of - and Metacyclophanes
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The synthesis and structure of - and metacyclophanes 2, 4 are described.The reductive ring opening of the thiophene rings of metacyclo(2,4)- and -(2,5)thiophenophanes 1 and 3 by Raney-Ni affords the corresponding - and metacyclophanes 2
- Takeshita, Michinori,Tsuge, Akihiko,Tashiro, Masashi
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p. 411 - 413
(2007/10/02)
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- Cyclophanes, XXI. The Chemical Behavior of Paracyclophane: Reactions of the Benzene Ring
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Preparative quantities of paracyclophane (1b) may be prepared from paracyclophane-3,6-dione (9) by Wolff-Kishner reduction.After a detailed dicussion of the 1H and 13C NMR spectra of 1b, its behavior in substitution and addition reactions is describ
- Noble, Karl-Ludwig,Hopf, Henning,Ernst, Ludger
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p. 455 - 473
(2007/10/02)
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- Arenes Disubstituted with Primary Alkyl Groups from Xylylene Dianions
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Xylenes were converted into dianions 1.Reaction of dianions 1 with dialkyl sulfates gave symmetrical dialkylbenzenes 2 (R = R'), while methyl iodide caused oxidative coupling followed by alkylation to give 8.Unsymmetrical dialkylbenzenes 2 (R =/= R') were made by an indirect route involving monoanions 9 and 11.Reactions of dianions 1 with dihalides gave cyclophanes o-3 (n = 5,6,9), m-3 (n = 8-10), and p-3 (n = 9-11) and cyclophanes o-4 (n = 2,5,7,9) and m-4 (n = 2,6,7).Dianion 5 from 2,6-lutidine was used to prepare nitrogen analogues of 2 (R = R') and m-3 (n = 8-10).
- Bates, Robert B.,Ogle, Craig A.
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p. 3949 - 3952
(2007/10/02)
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