35324-46-0Relevant academic research and scientific papers
Organic halogenation chemistry as a vital tool for the construction of functional π-conjugated materials
Tovar, John D.
, p. 2387 - 2391 (2011/09/21)
Recent and ongoing efforts by the Tovar research group to exploit organic halogenation chemistry for the development of complex organic electronic materials are described. Standard synthetic approaches involving free-radical and electrophilic reaction pathways are presented along with strategies that use ionizable protons or triazenes as masking groups for aromatic halides. Forward synthetic processes that highlight the extended chemistry that can be applied to these halogenated substrates to give complex π-conjugated molecules are also discussed. The examples presented are specific to work from the groups laboratories, but the halogenation procedures are sufficiently general to be suitable for use on many other conjugated frameworks. Georg Thieme Verlag Stuttgart New York.
Radical cascade transformations of tris(o-aryleneethynylenes) into substituted benzo[a]indeno[2,1-c]fluorenes
Alabugin, Igor V.,Gilmore, Kerry,Patil, Satish,Manoharan, Mariappan,Kovalenko, Serguei V.,Clark, Ronald J.,Ghiviriga, Ion
supporting information; experimental part, p. 11535 - 11545 (2009/02/03)
Oligomeric o-aryleneethynylenes with three triple bonds undergo cascade radical transformations in reaction with a Bu3SnH/AIBN system. These cascades involve three consecutive cycle closures with the formation of substituted benzo[a]indeno[2,1-c]fluorene or benzo[1,2]fluoreno[4,3-b]silole derivatives. The success of this sequence depends on regioselectivity of the initial attack of the Bu3Sn radical at the central triple bond of the o-aryleneethynylene moiety. The cascade is propagated through the sequence of 5-exo-dig and 6-exo-dig cyclizations which is followed by either a radical attack at the terminal Ar substituent or radical transposition which involves H-abstraction from the terminal TMS group and 5-endo-trig cyclization. Overall, the transformation has potential to be developed into an approach to a new type of graphite ribbons.
PtCl2-catalyzed hydrative cyclization of trialkyne functionalities to form bicyclic spiro ketones
Chang, Hsu-Kai,Datta, Swarup,Das, Arindam,Odedra, Arjan,Liu, Rai-Shung
, p. 4744 - 4747 (2008/02/08)
(Chemical Equation Presented) Triple rounds: A regioselective hydrative cyclization of triynes has been developed to give bicyclic β-hydroxy spiro ketones, which undergo subsequent dehydration to give the β,γ- unsaturated ketones (see scheme). Model reactions suggest that this platinum catalysis includes two selective hydrations, an alkyne insertion, and an aldol condensation.
Double elimination protocol for convenient synthesis of dihalodiphenylacetylenes: Versatile building blocks for tailor-made phenylene-ethynylenes
Orita, Akihiro,Miyamoto, Kazuhiko,Nakashima, Mikio,Ye, Fangguo,Otera, Junzo
, p. 767 - 776 (2007/10/03)
Dihalodiphenylacetylenes are conveniently synthesized by a double elimination reaction of β-substituted sulfones which are readily obtained from halogen-substituted benzyl sulfone and benzaldehyde derivatives. Halogens can be incorporated at any desired positions in the diphenylacetylene skeleton simply by choosing the substitution position of the halogen on the aromatic rings of the starting compounds. The diphenylacetylenes with different halogen substituents thus obtained undergo sequential carbon-carbon bond formations due to the different reactivities of the halogens. Thus, various moieties can be incorporated on the diphenylacetylene skeleton at whichever positions so that a variety of tailor-made phenylene-ethynylenes with regulated structure and composition could be designed.
Generation and characterization of highly strained dibenzotetrakisdehydro[12]annulene
Tobe, Yoshito,Ohki, Ichiro,Sonoda, Motohiro,Niino, Hiroyuki,Sato, Tadatake,Wakabayashi, Tomonari
, p. 5614 - 5615 (2007/10/03)
We report here the generation of tetrakisdehydro[12]annulene possessing a highly deformed triyne component from the [4.3.2]propellatriene-annelated precursor by its photolysis extruding indan and the characterization of the highly reactive annulene by che
