85545-64-8Relevant academic research and scientific papers
DIENE-TRANSMISSIVE DIELS-ALDER CYCLOADDITION REACTION OF BIS(SILYLOXY) CROSS-CONJUGATED TRIENES.
Tsuge,Wada,Kanemasa,Sakoh
, p. 3221 - 3233 (1984)
Multiple Diels-Alder reaction of bis(silyloxy) cross-conjugated trienes is presented. Two trienes, 3-benzylidene- and 3-(methoxymethylene)-2,4-bis(trimethylsilyloxy)-1,4-pentadiene, undergo two sequential Diels-Alder cycloadditions with a variety of dieno
Cycloaddition of [3]dendralene derivatives to dinitrobenzofuroxan and nitrobenzodifuroxan
Morozov, Pavel G.,Kurbatov, Sergey V.,Semenyuk, Yulia P.,Burov, Oleg N.,Kletskii, Mikhail E.,Fedik, Nikita S.,Suzdalev, Konstantin F.
, p. 903 - 912 (2015)
It has been show experimentally (by NMR spectroscopy and X-ray structural analysis) and theoretically (by quantum-chemical calculations according to DFT with B3LYP/6-31G basis set) that the cycloaddition of [3]dendralene derivatives to nitrobenzodifuroxan and dinitrobenzofuroxan occurs by a stepwise mechanism with a σ-complex as intermediate. It was shown that the cycloaddition steps occurring contrary to the Alder endo rule are characterized by significant global electrophilicity index differences for the reagents (Δω> 3.0 eV). The stages with Δω ≤ 3.0 eV occurred in accordance with the Alder endo rule as concerted processes. X-ray structural analysis and quantum-chemical calculations within the framework of AIM model identified intramolecular attraction forces between non-bonded atoms in the cycloadduct of phenyldendralene and nitrobenzodifuroxan.
3-BENZYLIDENE-2,4-BIS(TRIMETHYLSILYLOXY)-1,4-PENTADIENE; SYNTHESIS AND ITS DIENE-TRANSMISSIVE DIELS-ALDER REACTION
Tsuge, Otohiko,Wada, Eiji,Kanemasa, Shuji
, p. 239 - 242 (2007/10/02)
A novel cross-conjugated triene, 3-benzylidene-2,4-bis(trimethylsilyloxy)-1,4-pentadiene, was synthesized and the multiple Diels-Alder cycloaddition reactions to acetylenic dienophiles leading to the dihydronaphthols were demonstrated.
