5628-16-0Relevant articles and documents
[2.2]Paracyclophane-4,7,12,15-tetrone, [2.2](1,4)naphthalenophane-4,7,14,17-tetrone, and 1,4,8,11-pentacenetetrone radical anions - A comparative ESR study
Wartini, Alexander R.,Valenzuela, Jorge,Staab, Heinz A.,Neugebauer, Franz A.
, p. 221 - 227 (1998)
Three types of tetrone radical anions in which two 1,4-benzoquinone units are connected by ethano (1·-, 2·-), [2.2]paracyclophane (3·-, 4·-), and anthracene bridges (5·-, 6·-) have been studied by ESR and ENDOR spectroscopy. The displacement of the unpaired electron over the two π moieties in the [2.2]cyclophane radical anions 1·--4·- and the marked difference between the first and second reduction potentials, ΔE = |E2° - E1°| ≥ 0.20 V, are evidence for a substantial intramolecular electronic interaction between the two electrophores. Similar ΔE data for the syn- (3) and anti-naphthalenophanes (4) indicate that most of the intramolecular electronic interaction takes place through the [2.2]paracyclophane bridge. When ion pairing is inhibited by complexation of the cation, the unpaired electron in 5·- and 6·- is also delocalized over the whole pentacenetetrone system at temperatures as low as 160 K.
Phenyliodine diacetate-mediated para-functionalizations of amido- and amino-substituted [2.2]paracyclophanes
Schaal, Petra,Baars, Hannah,Raabe, Gerhard,Atodiresei, Iuliana,Bolm, Carsten
supporting information, p. 2506 - 2512 (2013/10/21)
The reaction of N-[2.2]paracyclophanyl-substituted amides or amines with phenyliodine diacetate (PIDA) and protic nucleophiles affords mixed para-substituted [2.2]paracyclophane derivatives in moderate to good yields. As protic nucleophiles carboxylic aci
Modular synthesis of planar-chiral para-substituted paracyclophanes by double Suzuki coupling
Cakici, Murat,Braese, Stefan
, p. 6132 - 6135 (2013/01/15)
The first synthesis of enantiomerically pure 4,7-paracyclophane ditriflate starting from a quinone was reported. Using this molecule, mono-or dicoupling with boronic acids delivered enantiomerically pure arylparacyclophanes.
Hemicarcerands that encapsulate hydrocarbons with molecular weights greater than two hundred
Cram, Donald J.,Jaeger, Ralf,Deshayes, Kurt
, p. 10111 - 10116 (2007/10/02)
Syntheses are reported for the globe-shaped hemicarcerands 1 and 2 composed of two rigid bowl-like units (polar caps) attached to one another at their rims through four OCH2C≡CC≡CCH2O units (equatorial spacers). Eight pendant CH3(CH2)4 groups in 1 and C6H5CH2CH2 groups in 2 attached in assemblies of four to each polar cap render the hosts soluble in organic solvents. The important shell-closing reactions 2Ar(OCH2C≡CH)4 + [O] → Ar(OCH2C≡CC≡CCH2O)4Ar went in 5-8% yields in pyridine-O2-Cu(OAc)2 to give a hemicarcerand free of pyridine. The higher solubility of 1 (compared to that of 2) in organic solvents led to an examination of its binding properties. By heating 1 dissolved either in potential guests or in 1,3,5-[(CH3)3C]3C6H3 (too large to enter 1) containing dissolved potential guests at 80-140 °C for 2-7 days, 1:1 hemicarceplexes mixed with the empty host were isolated in those cases when the potential guests were just small enough to enter the host's portals at high temperatures but large enough not to depart during isolation as stable solids. Thus, constrictive bonding played a large role in kinetic stabilization of the hemicarceplexes. The 1H NMR spectra of both the host and the guest were markedly modified upon complexation. The half-lives in hours of representative complexes dissolved in CDCl3 at 25 °C were as follows: 1·1,3,5-[(CH3)2CH]3C6H 3, 1628; 1·1,3,5-Et3C6H3, 960; 1·4-Et[2.2]paracyclophane, 24; 1·1,3-dimethyladamantane, 13.5; 1-[3.3]paracyclophane, 13; 1·tetradehydro[2.2]paracyclophane, 11; 1·[2.2]paracyclophane, 5; 1·4,12-dihydroxy[2.2]paracyclophane, 4; and 1·[2.3]paracyclphane, 0.5. Complexes of smaller guests such as CHCl3, ferrocene, adamantane, and 1,3,5-trimethylbenzene were unstable to room-temperature isolation conditions. Larger guests such as [3.4]paracyclophane and 4,12-dinitro[2.2]paracyclophane did not enter the portals of 1 at temperatures under which host 1 was stable, whereas smaller guests such as CH2Cl2 and pyridine entered and departed the host at 25 °C rapidly on the NMR time scale. Catalytic reduction (H2, PdC) of the eight acetylenic bonds of 1 produced an empty host of much more flexible structure, 3, whose binding properties have not yet been examined.
Treatment of Dimethoxyparacyclophanes with Ammonium Cerium(IV) Nitrate
Takeshita, Michinori,Tsuzuki, Hirohisa,Tashiro, Masashi
, p. 2076 - 2082 (2007/10/02)
The treatment of dimethoxyparacyclophanes (n=7-12) (5), paracyclothiophenophane (13), and dimethoxyparacyclophane (8) with CAN in MeCN-water afforded 2,4-cyclohexadien-1-ones 9, paracyclophanedione 10, the ring-opened esters 11, and keton
SYNTHESIS OF o-BENZOQUINONES DERIVED FROM - AND PRACYCLOPHANES
Miyahara, Yuji,Inazu, Takahiko,Yoshino, Tamotsu
, p. 2189 - 2190 (2007/10/02)
Oxidation of - and paracyclophanols with benzeneseleninic anhidride readily afforded the corresponding cyclophane-o-quinones which showed the intramolecular charge-transfer interactions.
