Synthesis and Fragmentation of Furoxanaldehydes in the Gas Phase for Nanopatterned Alkyne Formation on a Solid Surface
- Authors
- Kim, Gi Young; Kim, Jucheon; Lee, Seung Hee; Kim, Hyung Jin; Hwang, Kwang-Jin
- Issue Date
- 20-Feb-2009
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- Alkyne; Furoxan; Furoxanaldehyde; E-beam; Fragmentation
- Citation
- BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v.30, no.2, pp.459 - 463
- Journal Title
- BULLETIN OF THE KOREAN CHEMICAL SOCIETY
- Volume
- 30
- Number
- 2
- Start Page
- 459
- End Page
- 463
- URI
- https://scholarworks.bwise.kr/hongik/handle/2020.sw.hongik/21906
- ISSN
- 0253-2964
- Abstract
- Furoxanaldellydes 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 NaNO2 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 I 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 diaryl-acetylene at high efficiency, suggesting that the aryl group conjugated with the furoxan ring could facilitate alkyne formation with the evolution of NO.
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