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http://dx.doi.org/10.5012/bkcs.2009.30.2.459

Synthesis and Fragmentation of Furoxanaldehydes in the Gas Phase for Nanopatterned Alkyne Formation on a Solid Surface  

Kim, Gi-Young (Department of Chemical System Engineering, Hongik University)
Kim, Ju-Cheon (Department of Chemical System Engineering, Hongik University)
Lee, Seung-Hee (Department of Chemical System Engineering, Hongik University)
Kim, Hyung-Jin (Center for Functional Nano Fine Chemicals, School of Applied Chemical Engineering, Chonnam National University)
Hwang, Kwang-Jin (Department of Chemical System Engineering, Hongik University)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.2, 2009 , pp. 459-463 More about this Journal
Abstract
Furoxanaldehydes possessing phenyl or alkenyl groups at the 3- or 4-position of the furoxan ring were designed for alkyne formation on a solid surface. Furoxans 2 and 3 were prepared from the corresponding alkenes 2a and 3a by the reaction with NaN$O_2$ in acetic acid. Furoxan 4, in which the furoxan ring is conjugated with a double bond, was prepared from bis(bromomethyl)benzene 4a in 5 steps using the Wittig reaction of aldehyde 1 as the key step. The electron beam-mediated fragmentation of furoxanaldehydes 1-4 in a mass spectrometer was exploited by focusing on alkyne formation on the solid surface. The fragmentation of furoxan 3 possessing diaryl groups afforded diarylacetylene at high efficiency, suggesting that the aryl group conjugated with the furoxan ring could facilitate alkyne formation with the evolution of NO.
Keywords
Alkyne; Furoxan; Furoxanaldehyde; E-beam; Fragmentation;
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