31183-16-1Relevant academic research and scientific papers
Direct observation of change in the molecular structure of benzyl (Z,Z)-muconate during photoisomerization in the solid state
Furukawa, Daisuke,Kobatake, Seiya,Matsumoto, Akikazu
, p. 55 - 57 (2008)
For the solid-state photoisomerization of benzyl (Z,Z)-muconate to the corresponding (E,E)-muconate, the direct observation of a change in the crystal structure has revealed that the isomerization occurs by a topochemical reaction process according to a b
Single-crystal-to-single-crystal transformation of Di(isopropylammonium) (Z,Z)-muconate into the (E,E)-muconate during one-way photoisomerization in the solid state
Nishizawa, Natsuko,Nakamura, Junya,Matsumoto, Akikazu
, p. 3442 - 3447 (2011)
The solid-state EZ photoisomerization of di(isopropylammonium) (Z,Z)-muconate (ZZ-1a) into the corresponding EE isomer (EE-1a) via a single-crystal-to-single-crystal reaction process was investigated. The molecular motion based on a bicycle-pedal model wa
Crystal phase transition and solid-state photoisomerization of benzyl (Z,Z)-muconate polymorphs studied by direct observation of crystal structure change
Nishizawa, Natsuko,Furukawa, Daisuke,Kobatake, Seiya,Matsumoto, Akikazu
, p. 3203 - 3210 (2010)
We investigated the polymorph structures of benzyl (Z,Z)-muconate crystals (ZZ-Bn-α, β, and γ) and their EZ photoisomerization behavior in order to clarify the EZ isomerization mechanism of diene compounds in the solid state. First, the thermodynamics and crystal phase transition of the polymorphs were investigated by differential scanning calorimetry and X-ray diffraction. A single-crystal-to-single-crystal transition was observed during the change in the polymorph structures from the ZZ-Bn-β to the α form. We also observed in situ the migration of the boundary between the different polymorph domains during the phase transition of the ZZ-Bn-γ to the r form by optical microscopy. We then investigated the change in the crystal structure of ZZ-Bn during the EZ photoisomerization in the solid state. The photoisomerization of ZZ-Bn to the corresponding EE isomer (EE-Bn) proceeded according to a bicycle-pedal model via a single-crystal-to-single-crystal topochemical reaction mechanism, which was directly confirmed by an X-ray single-crystal structure analysis. During the photoirradiation of the polymorph crystals of ZZ-Bn-α and β, a structural strain was accumulated in the crystal lattice and finally caused a phase transition accompanied by a change in the space group from P21/c to P21, resulting in a stable crystal structure identical to that of the recrystallized EE-Bn. On the other hand, the ZZ-Bn-γ crystals became amorphous during the photoirradiation because of the greater molecular motions in the crystals. Thus, we have demonstrated the validity of the in situ single-crystal structure analysis for investigating the EZ photoisomerization of diene compounds in the solid state.
Ruthenium-catalysed oxidative coupling of vinyl derivatives and application in tandem hydrogenation
Abuhafez, Naba,Bruneau, Christian,Gramage-Doria, Rafael,Kamaraj, Raghu,Ruffin, Hervé
, p. 5772 - 5776 (2021/09/10)
The first ruthenium-catalyzed oxidative homo- and cross-coupling of exclusive vinyl derivatives giving highly valued 1,3-diene building blocks is reported. The catalytic system is based on readily available reagents and it mainly delivers the E,E isomer. This methodology also enables the synthesis of adipic acid ester derivatives in a one-pot fashion after in situ ruthenium-catalyzed hydrogenation.
Crystal engineering for topochemical polymerization of muconic esters using halogen-halogen and CH/π interactions as weak intermolecular interactions
Matsumoto, Akikazu,Tanaka, Toshihiro,Tsubouchi, Takashi,Tashiro, Kohji,Saragai, Seishi,Nakamoto, Shinsuke
, p. 8891 - 8902 (2007/10/03)
We now report the molecular and crystal structure design of muconic ester derivatives on the basis of crystal engineering using halogen-halogen contacts and CH/π interactions. The solid-state photoreaction pathway of the dibenzyl (ZZ)-muconates as the 1,3
Reaction of Aryl and Vinyl Halides with Zerovalent Nickel-Preparative Aspects and the Synthesis of Alnusone
Semmelhack, M.F.,Helquist, Paul,Jones, L.D.,Keller, Leonard,Mendelson L.,et al.
, p. 6460 - 6471 (2007/10/02)
Zerovalent nickel complexes such as bis(1,5-cyclooctadiene)nickel and tetrakis(triphenylphosphine)nickel react rapidly with aryl and vinyl halides to produce the symmetrical coupling products, a low-temperature analogue of the Ullman reaction.The reaction proceeds through oxidative addition of the organic halide to Ni(0), and the reactivity of the Ni(II)intermediates has been examined.Arylnickel halide complexes decompose rapidly to biaryls in DMF.The coupling of simple vinyl halides proceeds with isomerization of the double bond but 3-haloacrylates give efficient co upling with retention of geometry.Cyclizations to form ortho-bridged biaryls are efficient in simple cases (6-, 7-, 8-, 9-, 10-, and 14-membered rings) but fail with an ortho-disubstituted case.The 13-membered meta-bridged cyclic biphenyl, alnusone, is prepared efficiently with the crucial aryl halide coupling to form the ring proceeding in 50percent yield.A side reaction promoted by the presence of protons and with certain ortho-substituted aryl halides is reduction of the aryl halide to the arene.This process can be enhanced by deliberate addition of acid during reaction with Ni(0) and a series of aryl halides underwent succesful reduction.
