83759-89-1Relevant academic research and scientific papers
Design, preparation, X-ray crystal structure, and reactivity of o-alkoxyphenyliodonium bis(methoxycarbonyl)methanide, a highly soluble carbene precursor
Zhu, Chenjie,Yoshimura, Akira,Ji, Lei,Wei, Yunyang,Nemykin, Victor N.,Zhdankin, Viktor V.
supporting information; experimental part, p. 3170 - 3173 (2012/08/07)
The preparation, X-ray structure, and reactivity of new, highly soluble, and reactive iodonium ylides derived from malonate methyl ester and bearing an ortho substituent on the phenyl ring are reported. These new reagents show higher reactivity than common phenyliodonium ylides in the Rh-catalyzed cyclopropanation, C-H insertion, and transylidation reactions under homogeneous conditions.
On the most powerful chemical traps for bis(methoxycarbonyl)carbene (=2-methoxy-1-(methoxycarbonyl)-2-oxoethylidene)
Shevchenko, Vladimir V.,Zhegalova, Natalya G.,Borzenko, Andey O.,Nikolaev, Valerij A.
experimental part, p. 501 - 509 (2009/02/07)
The efficiency and validity of different chemical substrates for trapping bis(methoxycarbonyl)carbene (=2-methoxy-1-(methoxycarbonyl)-2-oxoethylidene; 1) is dependent on the conditions of carbene generation. On conventional photolysis of dimethyldiazomalonate (=2-diazopropanedioic acid dimethyl ester; 2) by long-wave UV light (through a Pyrex filter, λ > 290 nm), the most powerful trap for carbene 1 in the series of substrates Me2S, MeOH, cyclohexane, and pyridine is Me2S (with an efficiency ratio of ca. 6 :4 : 2 : 1, resp.). When short-wave decomposition of diazomalonate 2 is employed (through a quartz filter, λ > 210 nm), more reliable and useful chemical traps for bis(methoxycarbonyl)carbene (1) are pyridine and cyclohexane, whose adducts with 1 are rather stable under short-wave-irradiation conditions. Application of alcohols for the trapping of 1 proves to be preferential when simultaneous monitoring of carbene and oxoketene formation during photolysis is necessary.
