38717-96-3Relevant academic research and scientific papers
Synthesis of Azulen-1-yl Ketones via Oxidative Cleavage of C-C Multiple Bonds in N-Sulfonyl Enamides and 1-Alkynes under Air and Natural Sunlight
Park, Sangjune,Jeon, Woo Hyung,Yong, Woo-Soon,Lee, Phil Ho
supporting information, p. 5060 - 5063 (2015/11/03)
A synthetic method to prepare azulen-1-yl ketones was developed via oxidative cleavage of the C-C double bond in the reaction of easily obtainable N-sulfonyl enamides with Cs2CO3 under air and natural sunlight and in the absence of a photosensitizer. Oxidative cleavage of C-C triple bonds was also demonstrated for the synthesis of azulen-1-yl ketones via a tandem Cu-catalyzed [3 + 2] cycloaddition, Rh-catalyzed arylation, photooxygenation, and ring-opening reaction in one pot under air and natural sunlight.
Synthesis and intramolecular pericyclization of 1-azulenyl thioketones
Ito, Shunji,Okujima, Tetsuo,Kikuchi, Shigeru,Shoji, Taku,Morita, Noboru,Asao, Toyonobu,Ikoma, Tadaaki,Tero-Kubota, Shozo,Kawakami, Jun,Tajiri, Akio
, p. 2256 - 2263 (2008/09/19)
Several azulene-substituted thioketones, 1-thiobenzoylazulene (1a) and di(1-azulenyl) thioketone (2a) and their derivatives (1b and 2b-d) with alkyl substituents on each azulene ring, were prepared and their intramolecular pericyclization reaction was exa
ALKYLATION AND ACYLATION OF AZULENE IN THE PRESENCE OF COPPER
Nefedov, V. A.,Tarygina, L. K.
, p. 1724 - 1728 (2007/10/03)
In the presene of copper powder organic halogen derivaties react with azulene to form 1-R- and 1,3-R2-=azulenes.The acid chlorides are most active in the series R = PhCO, PhCH=CHCO, Me2NCO, PhCH2, H2CCCH2, Bu, and EtOOCCH2.With copper phenylacetylide (insted of copper) it is possible to obtain allyl- and propargylazulenes with high yields under mild conditions.In reaction with copper and azulene aryl halides dimerize to ArAr, but thhey do not substitute hydrogen in the azulene.
OXIDATIVE SUBSTITUTION XIV. SUBSTITUTION OF HALOGEN IN AROMATIC RING. NEW THEORIES ABOUT THE MECHANISM OF THE ACTION OF CuX2
Nefedov, V.A.,Tarygina, L.K.,Kryuchkova, L.V.,Ryabokobylko, Yu.S.
, p. 487 - 499 (2007/10/02)
The stoichiometry, the comparative reactivity of halogens and hydrogen, the effect of substituents, and the action of an additional oxidizing agent were determined for the reactions of halogenoazulenes with CuX2., leading to substitution of the halogen by the group X (X = Cl, Br, SCN, SeCN, NO2, SO2, Ph).According to model experiments, the equilibrium CuX2 + CuX+ X+ + 2CuX is possible.The reaction of Cu(SO2Ph)2 with Cu(BF4)2 leads to the formation of two equivalents of a copper(I) salt; short-lived particles which substitute the hydrogen and halogen in the substrate are generated during the reaction.It is suggested that the electron generated during oxidation or autooxidation of CuX2 is capable of combining with the substrate.New methods were found for the synthesis of azulene derivatives, and known methods were improved.
