904368-96-3Relevant academic research and scientific papers
Synthesis and stability of 1,1-dialkyl-1H-azulenium cations
Oda, Mitsunori,Nakajima, Nobue,Thanh, Nguyen Chung,Kajioka, Takanori,Kuroda, Shigeyasu
, p. 8177 - 8183 (2006)
Starting from trimethylsilyl enol ether of 1-acetyl-1,3,5-cycloheptatriene, the title 1,1-dimethyl-, 1,1-diethyl-, and 1,1-dipropyl-1H-azulenium cations 6-8 were synthesized in five steps. The order of pKR+ values of these cations was found to be 7>8>6. A comparison of the values between 1,1-dialkyl- and 1,1-spiroalkylated 1H-azulenium cations with the same number of carbon atoms at the 1-position provided the results of 7>1 and 8R+ value to those of 3 and 7 probably due to its slightly bulkier propyl groups from which solvation stabilization of 8 under the conditions suffers. An intermolecular charge-transfer interaction between the cations and dibenzo-24-crown-8 was also studied.
