26154-65-4Relevant academic research and scientific papers
1,1-Ethylene-1H-azulenium ion and its alkyl substituted derivatives: Synthesis, characterization, and some reactions thereof
Oda, Mitsunori,Kajioka, Takanori,Uchiyama, Takuya,Nagara, Kohki,Okujima, Tetsuo,Ito, Shunji,Morita, Noboru,Sato, Toshio,Miyatake, Ryuta,Kuroda, Shigeyasu
, p. 6081 - 6096 (1999)
1,1-Ethylene-1H-azulenium tetrafluoroborate (1b) and its alkyl substituted derivatives, 6-t-butyl (1c) and 4-isopropyl-3,8-dimethyl ones (Id), were synthesized starting from their corresponding azulenes by a three- step sequence which includes reduction, cyclopropanation and hydride abstraction reactions. The cation 1b and its 6-t-butyl derivative 1c, generated in deuterated acetonitrile at -20 °C, were characterized by low- temperature NMR spectroscopy. On the other hand, the cation Id was isolated os slightly unstable, greenish-yellow crystals. While the cation 1b in solution underwent expansion of the cyclopropane ring at elevated temperatures, 1c and 1d just decomposed. All the cations were found to react easily with nucleophiles to give thermodynamically controlled, stable addition products at their cyclopropane methylene carbons.
Generation, characterization and some reactions of 1,1-ethylene-1H-azulenium ion
Oda, Mitsunori,Kajioka, Takanori,Okujima, Tetsuo,Itoh, Shunji,Morita, Noboru,Miyatake, Ryuta,Kuroda, Shigeyasu
, p. 1011 - 1012 (1997)
The title carbocation, generated from 1,1-ethylene-1,6-dihydroazulene and trityl tetrafluoroborate in deuterated acetonitrile at - 20°C, was characterized by means of low temperature NMR spectroscopy, and was found to undergo expansion of the cyclopropane ring at elevated temperature and to react with nucleophiles to give the addition products at the cyclopropane methylene carbon.
Addition reaction of cyclic ethers to 1,1-ethylene-1H-azulenium ion
Oda, Mitsunori,Uchiyama, Takuya,Kajioka, Takanori,Hashimoto, Tomomi,Miyatake, Ryuta,Kuroda, Shigeyasu
, p. 2071 - 2077 (2007/10/03)
The title cation (1) was found to react with some cyclic ethers in the presence of sodium acetate and acetic acid to give the products derived from nucleophilic addition of the ether oxygen atom at the three-membered ring methylene carbon of 1.
