- Base-controlled divergent synthesis of vinyl sulfones from (benzylsulfonyl)benzenes and paraformaldehyde
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A tuneable metal-free protocol for the selective preparation of a-substituted vinyl sulfone and (E)-vinyl sulfone derivatives has been described. In this process, stable paraformaldehyde was used as the carbon source. The base played an important role in the selectivity control of transformations. More than 50 products were synthesized with excellent chemoselectivity and broad functional group tolerance.
- Xiao, Fuhong,Hu, Yangling,Huang, Huawen,Xu, Fen,Deng, Guo-Jun
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supporting information
p. 3527 - 3535
(2020/05/25)
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- A visible-light photoactivatable di-nuclear PtIV triazolato azido complex
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A novel PtIV triazolato azido complex [3]-[N1,N3] has been synthesised via a strain-promoted double-click reaction (SPDC) between a PtIV azido complex (1) and the Sondheimer diyne (2). Photoactivation of [3]-[N1,N3] with visible ligh
- Yao, Kezi,Bertran, Arnau,Howarth, Alison,Goicoechea, Jose M.,Hare, Samuel M.,Rees, Nicholas H.,Foroozandeh, Mohammadali,Bowen, Alice M.,Farrer, Nicola J.
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supporting information
p. 11287 - 11290
(2019/09/30)
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- MULTICYCLIC AROMATIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME
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The present specification describes a multicyclic aromatic ring compound having a novel structure and an organic light emitting device using the same.
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Paragraph 0137-0140
(2017/04/21)
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- Cyclopropenone-caged Sondheimer diyne (dibenzo[a,e]cyclooctadiyne): A photoactivatable linchpin for efficient SPAAC crosslinking
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The first fully conjugated bis-cyclopropenone (photo-DIBOD), a derivative of dibenzo[a,e][8]annulene, has been synthesized. 350-420 nm irradiation of this robust compound results in the efficient formation of dibenzo [a,e] cyclooctadiyne, an unstable, but
- Sutton, Dewey A.,Yu, Seok-Ho,Steet, Richard,Popik, Vladimir V.
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supporting information
p. 553 - 556
(2016/01/09)
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- Substituted 5,6,11,12-tetradehydrodibenzo[ a, e ]cyclooctenes: Syntheses, properties, and DFT studies of substituted sondheimer-wong diynes
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Highly strained cyclic acetylenes 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctenes (Sondheimer-Wong diynes) having various substituents on their benzene rings were synthesized successfully by one-pot treatment of the corresponding formyl sulfones with diethyl chlorophosphate/lithium hexamethyldisilazide (LiHMDS) and then lithium diisopropylamide (LDA). When mixtures of two types of formyl sulfones bearing different substituents were subjected to this protocol, the unsymmetrically substituted Sondheimer-Wong diynes could be synthesized in a stepwise manner by isolation of the heterocoupled vinyl sulfone intermediates followed by their treatment with LDA. The UV-vis absorption spectra and cyclic voltammograms of the substituted Sondheimer-Wong diynes were recorded. The electronic effect of substituents on the diynes was investigated in their click reactions and nucleophilic and electrophilic additions.
- Xu, Feng,Peng, Lifen,Shinohara, Kenta,Morita, Takamoto,Yoshida, Suguru,Hosoya, Takamitsu,Orita, Akihiro,Otera, Junzo
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p. 11592 - 11608
(2015/01/09)
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- Double elimination protocol for synthesis of 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctene
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A new method for constructing 5,6,11,12-tetradehydrodibenzo[a,e]-cyclooctene is described on the basis of one-pot double elimination protocol. The target molecule, which is the smallest cyclophane with alternate arylene-]ethynylene linkage, is synthesized in 61% yield through oxidative dimerization of ortho-(phenylsulfonylmethyl)-benzaldehyde. The initial carbon-carbon bond formation between sp3 carbons followed by stepwise conversion to sp2 and finally sp carbons bypasses the difficulty encountered in direct coupling of the sp carbon in the terminal acetylene. The mechanism of this process is discussed. The Wittig-Horner-type coupling is a key reaction employed for the carbon-carbon bond formation. Generation of (E)-vinylsulfone moiety in the first coupling between a-sulfonyl anion and aldehyde functions is crucial for the effective second coupling to complete the cyclization. The syn-elimination of the (E)-vinylsulfone moieties in the cyclized intermediate furnishes the acetylenic bonds.
- Orita, Akihiro,Hasegawa, Daiki,Nakano, Takehiko,Otera, Junzo
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p. 2000 - 2004
(2007/10/03)
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- α-(METHYLTHIO)BENZYL SULFONES AS SYNTHETIC INTERMEDIATES. PART IV. SOME NEW o-,m- AND p-SUBSTITUTED α-(METHYLTHIO)- AND α,α'-BIS-(METHYLTHIO)-BENZYL SULFONES
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The reaction of the meta nitro, methoxy and cyano substituted benzylic sulfones with an excess of dimethyl disulfide in the presence of NaH/DMSO, affords the corresponding α-monosulfenylated derivatives.However, no reaction occurs with the corresponding o-substituted sulfones.A new procedure is developed using S-methyl methanethiosulfonate, in excess, in the "phase transfer condition" which lead for the o-nitro and o-methoxy substituted sulfones to the α-monosulfenylated derivatives and for the o-cyano as well as p- and m-nitro, m-methoxy and m-cyano substituted benzylic sulfones to the correponding α,α'-bis-sulfenylated derivatives.
- Wladislaw, B.,Marzorati, L.,Ebeling, G.
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p. 163 - 167
(2007/10/02)
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