136809-45-5Relevant academic research and scientific papers
Direct CC Triple Bond Formation from the C=C Double Bond and Direct Hydroxylation into the o-Position of a Nitro Group on the Benzene Nucleus with Potassium t-Butoxide in N,N-DImethylformamide in the Air
Akiyama, Shuzo,Tajima, Kunihiko,Nakatsuji, Shin'ichi,Nakashima, Kenichiro,Abiru, Kazuko,Watanabe, Miwa
, p. 2043 - 2052 (2007/10/03)
A novel and facile method for direct CC acetylenic bond formation from the C=C double bond by treatment with potassium t-butoxide (t-BuOK) in N,N-dimethylformamide in the air has been found in a 9,10-bis(4-substituted styryl)anthracene series, in 4-substituted 4'-nitrostilbene series, and in 1-(p-nitrophenyl)-4-(p-substituted phenyl)-1,3-butadiene series; its scope and limitations have been examined.The ESR spectrum of the reaction against 4-diethylamino-4'-nitrostilbene was measured to identify an anion radical specied expected for explanation of the mechanism of the dehydrogention reaction.Further, cyclic voltammetric measurements of a series of stilbenes and diphenylacetylenes were carried out in connection with the abovw mechanism.In many cases, interestingly, the use of a large excess of t-BuOH brought about succeeding hydroxylation into the ortho-position of a nitro group on the benzene nucleus.The simple hydroxylation is useful for the synthesis of substituted 5-(arylethynyl)-2-nitrophenols, which are expected to function as non-linear optical materials with the corresponding non-hydroxy compounds.The ultraviolet-visible and fluorescence spectral properties were measured and discussed also with those of the related compounds.
Direct CC Triple Bond Formation from the C=C Double Bond with Potassium tert-Butoxide in Dimethylformamide containing Trace Amounts of Oxygen
Akiyama, Shuzo,Nakatsuji, Shin'ichi,Nomura, Kimiko,Matsuda, Kosei,Nakashima, Kenichiro
, p. 948 - 950 (2007/10/02)
A novel and facile method for direct acetylenic bond formation from the C=C double bond by treatment with KOBut in dimethylformamide has been found both in a 9,10-bis(4'-substituted styryl)anthracene series and in a 4-substituted 4'-nitro-stilb
