10541-38-5Relevant articles and documents
Palladium-Catalyzed Cross-Coupling Reaction of Organoboron Compounds with Organic Triflates
Oh-e, Takayuki,Miyaura, Norio,Suzuki, Akira
, p. 2201 - 2208 (1993)
The cross-coupling reaction of 9-alkyl-9-borabicyclononane (9-R-9-BBN), 1-alkenyl-1,3,2-benzodioxaborole, or aryl boronic acid with 1-alkenyl or aryl triflates in the presence of K3PO4 (1.5 equiv) and a catalytic amount of Pd(PPh3)4 or Cl2Pd(dppf) resulted in high yields.The reaction conditions are sufficiently mild so that a variety of functionalized alkenes, alkadienes, and arenes are readily obtained.The utility of the present reaction was demonstrated by the cyclization of ω-alkenyl triflates leading to a benzo-fused cycloalkene and bicyclic alkene via a hydroboration intramolecular coupling sequence.
Stereoretentive Ring-Opening Metathesis Polymerization to Access All- cis Poly(p-phenylenevinylene)s with Living Characteristics
Hsu, Ting-Wei,Kim, Cheoljae,Michaudel, Quentin
supporting information, p. 11983 - 11987 (2020/08/06)
Poly(p-phenylenevinylene)s (PPVs), a staple of the conductive polymer family, consist of alternating alkene and phenyl groups in conjugation. The physical properties of this organic material are intimately linked to the cis/trans configuration of the alkene groups. While many synthetic methods afford PPVs with all-trans stereochemistry, very few deliver the all-cis congeners. We report herein a synthesis of all-cis PPVs with living characteristics via stereoretentive ring-opening metathesis polymerization (ROMP). Exquisite catalyst control allows for the preparation of homopolymers or diblock copolymers with perfect stereoselectivity, narrow dispersities, and predictable average molar masses. All-cis PPVs can then serve as light-responsive polymers through clean photoisomerization of the stilbenoid units.
Alkyl substituted [2.2]paracyclophane-1,9-dienes
Lidster, Benjamin J.,Kumar, Dharam R.,Spring, Andrew M.,Yu, Chin-Yang,Helliwell, Madeleine,Raftery, James,Turner, Michael L.
supporting information, p. 6079 - 6087 (2016/07/06)
[2.2]Paracyclophane-1,9-dienes substituted with n-octyl chains have been synthesised from the corresponding dithia[3.3]paracyclophanes using a benzyne induced Stevens rearrangement. The use of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate and tetra-n-butylammonium fluoride as the in situ benzyne source gave significantly improved yields over traditional sources of benzyne and enabled the preparation of n-octyl substituted [2.2]paracyclophane-1,9-dienes on a multi-gram scale.
Selective synthesis of 1,4-dialkylbenzenes from terephthalic acid
Bramborg, Andrea,Linker, Torsten
supporting information; experimental part, p. 2195 - 2199 (2010/11/04)
Terephthalic acid reacts with alkyl halides under Birch conditions to substituted 1,4-cyclohexadienes in high yields and good stereoselectivities. Electrophiles containing ester or nitrile groups undergo a surprising fragmentation under the reaction conditions. Subsequent treatment with chlorosulfonic acid proceeds by an interesting tandem decarbonylationldecarboxylation, affording 1,4-dialkylbenzenes in excellent regioselectivity. Thus our new method is superior to classical Friedel-Crafts alkylations.
The preparations and some properties of mixed aryl-thienyl oligomers and polymers
Pelter, Andrew,Jenkins, Ieuan,Jones, D. Elfyn
, p. 10357 - 10400 (2007/10/03)
The syntheses by transition metal coupling reactions of a large number of oligomers constructed from benzene and thiophene rings are described. The first use of arylcadmium chlorides for such coupling reactions is reported. The routes chosen allow for rational variation in the modes of linkage, the substitution and the proportions of the two units. The benzene and thiophene rings are always joined in a known order and may bear a wide variety of regularly spaced functional groups. Additionally the shape of the oligomers may be varied at will. In all cases p-type doping with iodine or ferric chloride leads to large enhancements in conductivity.
SYNTHESIS AND SPECTROSCOPY OF 1,4-DIALKYLBENZENES
Issac, Yvette A.,El-Zein, S. M.,Barakat, Y.
, p. 463 - 470 (2007/10/02)
Five linear 1,3-dialkylbenzenes namely, dibutyl-, dipentyl-, dihexyl-, diheptyl- and dioctylbenzenes were prepared in good yield via two simple catalytic routes under very mild conditions and affording insignificant side products, The starting feed, 1,4-d
A High-Yield Route to 2,5-Di-n-alkyl-1,4-benzenedicarboxylic Acids
Rehahn, Matthias,Schlueter, Arnulf-Dieter,Feast, W. James
, p. 386 - 388 (2007/10/02)
A simple and inexpensive method for preparing the previously unknown 2,5-di-n-alkylterephthalic acids 5a-d in high yields is presented.The length of the alkyl chains can be varied easily (n=6,8,12,16).