Bridged Polycyclic Compounds. X. The Synthesis of endo and exo-1,2-Dihydrodicyclopentadienes and Related Compounds<sup>1</sup>

Cristol, Stanley J.; Seifert, Wolfgang; Soloway, Saul

doi:10.1021/ja01494a060

Cited by 52 publications

(23 citation statements)

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“…Novel cyclic olefin comonomers TUE and TTE are prepared via Diels‐Alder reaction of CPD with excess CHE and COE (cyclic olefin/CPD = 1.5), respectively, according the synthesis procedure of TDE reported in the previous literature with some modification . It is noteworthy that high temperature (200 °C) is critical to these reactions.…”

Section: Results and Disscusionmentioning

confidence: 99%

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Preparation of novel cyclic olefin copolymer with high glass transition temperature

Miao

Yang

Long

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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A series of novel cyclic olefin copolymers (COCs), including ethylene/tricyclo[4.3.0.12,5]deca‐3‐ene (TDE), ethylene/tricyclo[4.4.0.12,5]undec‐3‐ene (TUE), and ethylene/tricyclo[6.4.0.19,12]tridec‐10‐ene (TTE) copolymers, have been synthesized via effective copolymerizations of ethylene with bulk cyclic olefin comonomers using bis(β‐enaminoketonato) titanium catalysts (1a [PhNC(CH3)CHC(CF3)O]2TiCl2; 1b: [PhNC(CF3)CHC(Ph)O]2TiCl2). With modified methylaluminoxane as a cocatalyst, both catalysts exhibit high catalytic activities, producing high molecular weight copolymers with high comonomer incorporations and unimodal molecular weight distributions. The microstructures of obtained ethylene/COCs are established by combination of 1H, 13C NMR, 13C DEPT, HSQC 1H13C, and 1H1H COSY NMR spectra. DSC analyses indicate that the glass transition temperature (Tg) increases with the enhancement of comonomer volume (TDE < TUE < TTE). High Tg value up to 180 °C is easily attained in ethylene/TTE copolymer with the low content of 35.8 mol %. TGA analyses reveal that these copolymers all possess high thermal stability with degradation temperatures (Td) higher than 370 °C in N2 and air. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3144–3152

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Section: Results and Disscusionmentioning

confidence: 99%

“…The synthesis was carried out according to the procedure reported in the previous literature with some modification . Under nitrogen atmosphere, 126.0 g of CPD (1.90 mol), 193.8 g of CPE (2.85 mol), and 1 g of 2,6‐di‐tertbutyl‐ p ‐cresol were added to a 1 L autoclave.…”

Section: Methodsmentioning

confidence: 99%

Preparation of novel cyclic olefin copolymer with high glass transition temperature

Miao

Yang

Long

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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“…3 was prepared through a Diels-Alder reaction of cyclopentene and cyclopentadiene via the literature procedure. 15 endo-DCP (Acros), norbornene (Aldrich), and the other monomers were distilled and degassed (consecutive freeze-pump-thaw cycles) before use.…”

mentioning

confidence: 99%

ROMP Reactivity of endo- and exo-Dicyclopentadiene

Rule

Moore²

2002

Macromolecules

240

187

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The activation parameters for the ring-opening metathesis polymerization (ROMP) of endo-(1) and exo-dicyclopentadiene (2), endo-1,2-dihydrodicylopentadiene (3), and norbornene (4) in the presence of Grubbs' catalyst were determined using in situ NMR. The exo isomer of DCP was found to be more than an order of magnitude more reactive than the endo isomer. endo-DCP was found to have reactivity similar to its partially saturated counterpart 3, suggesting that the cause of the rate difference between the two isomers of DCP is primarily steric in nature. This interaction is shown to be predominantly entropic and is suspected to originate from an interaction of the penultimate repeat unit and the incoming monomer. Additionally, the alkylidene generated during the polymerization of endo-DCP was found to form an intramolecular complex, but this complex only affects the rate slightly.

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“…Racemic diastereomeric alcohols 5-8 were obtained following described procedures: O-exo,C-exo 5 (15); O-endo,C-exo alcohol 6 (16,17); O-exo,C-endo 7 (18); and O-endo,C-endo 8 (15,17,18) and characterized by comparison with reported spectroscopic data (17). FTIR spectra are reported in cm −1 .…”

Section: Methodsmentioning

confidence: 99%

“…General procedure for the synthesis of potassium xanthates (1)(2)(3)(4)(14)(15)(16)(17). The alcohol (1.1 eq) was slowly added to a solution of t-BuOK (1 eq.)…”

Section: Methodsmentioning

confidence: 99%

Synthesis and phospholipase C inhibitory activity of D609 diastereomers

González-Roura

Casas

Llebaría

2002

Lipids

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The potassium xanthate D609 is widely accepted as a selective inhibitor of PC-specific phospholipase C (PC-PLC). The tricyclo[5.2.1.(02,6)]decane skeleton present in D609 can lead to four diastereomeric pairs, but the diastereoselectivity of PC-PLC inhibition has never been reported. In this article, the synthesis of racemic D609 diastereomers and that of other xanthates, as well as their inhibitory effect on PC-PLC is reported. All xanthates obtained were competitive inhibitors of PC-PLC from Bacillus cereus (PLCBc). No significant differences were found in the activity of D609 diastereomers (Ki 13-17 microM), suggesting the absence of a diastereochemical control of the enzyme by xanthate inhibitors. This result was confirmed after obtaining other potassium xanthates differing from D609 in the aliphatic chain. Among them, the potassium O-n-decenylxanthate was the most active inhibitor of PLCBc (Ki 10 microM). These data indicate that the essential structural requirements for PLCBc in vitro inhibition by xanthates are the presence of a Zn-chelating dithiocarbonate head and a sufficiently hydrophobic aliphatic moiety.

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Bridged Polycyclic Compounds. X. The Synthesis of endo and exo-1,2-Dihydrodicyclopentadienes and Related Compounds¹

Cited by 52 publications

References 0 publications

Preparation of novel cyclic olefin copolymer with high glass transition temperature

Preparation of novel cyclic olefin copolymer with high glass transition temperature

ROMP Reactivity of endo- and exo-Dicyclopentadiene

Synthesis and phospholipase C inhibitory activity of D609 diastereomers

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Bridged Polycyclic Compounds. X. The Synthesis of endo and exo-1,2-Dihydrodicyclopentadienes and Related Compounds1

Cited by 52 publications

References 0 publications

Preparation of novel cyclic olefin copolymer with high glass transition temperature

Preparation of novel cyclic olefin copolymer with high glass transition temperature

ROMP Reactivity of endo- and exo-Dicyclopentadiene

Synthesis and phospholipase C inhibitory activity of D609 diastereomers

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Bridged Polycyclic Compounds. X. The Synthesis of endo and exo-1,2-Dihydrodicyclopentadienes and Related Compounds¹