24378-05-0Relevant academic research and scientific papers
Iron(III) Chloride Oxidation of Tricarbonyl(vinylketene)iron(0)-Alkyne Adducts
Saberi, Stephen P.,Salter, Matthew M.,Slawin, Alexandra M. Z.,Thomas, Susan E.,Williams, David J.
, p. 167 - 172 (1994)
Oxidation of the adducts formed from tricarbonyl(vinylketene)iron(0) complexes and alkynes by iron(III) chloride in methanol/water leads to the replacement of the tricarbonyliron(0) unit with an oxygen atom derived from the water.This pathway to furan-3(2H)-ones requires the presence of an electron-withdrawing substituent on carbon-2 of the vinylketene-alkyne adduct.Data used to assign the structures of some of the vinylketene-alkyne adducts used in this study included an X-ray crystal structure analysis of the unusual lactone complex 5c.
Decatungstate as Direct Hydrogen Atom Transfer Photocatalyst for SOMOphilic Alkynylation
Capaldo, Luca,Ravelli, Davide
, p. 2243 - 2247 (2021/04/05)
A versatile approach for the alkynylation of a variety of aliphatic hydrogen donors, including alkanes, is reported. We used tetrabutylammonium decatungstate as photocatalyst to generate organoradicals from C-H/Si-H bonds via hydrogen atom transfer. The l
Radical-mediated sulfonyl alkynylation, allylation, and cyanation of propellane
Wu, Zhen,Xu, Yaohui,Zhang, Huihui,Wu, Xinxin,Zhu, Chen
, p. 6066 - 6069 (2021/06/21)
Bicyclo[1.1.1]pentane (BCP) is widely applied as the bioisostere for aryl, internal alkynes, andtert-butyl groups in medicinal chemistry. We herein disclose an efficient and practical preparation of sulfonyl alkynyl/allyl/cyano-substituted BCP derivatives
Regiodivergent Rhodium(I)-Catalyzed Azide-Alkyne Cycloaddition (RhAAC) to Access Either Fully Substituted Sulfonyl-1,2,3-triazoles under Mild Conditions
Song, Wangze,Zheng, Nan,Li, Ming,Dong, Kun,Li, Junhao,Ullah, Karim,Zheng, Yubin
, p. 6705 - 6709 (2018/11/02)
A regiodivergent Rh(I)-catalyzed azide-alkyne cycloaddition (RhAAC) was developed for the synthesis of both fully substituted 4-sulfonyl-1,2,3-triazoles and 5-sulfonyl-1,2,3-triazoles in high regioselectivities and yields under mild conditions in one step
A practical synthesis of benzothiophenes via visible-light-promoted cyclization of disulfides and alkynes
Ye, Lin-Miao,Qian, Lu,Chen, Yan-Yan,Zhang, Xue-Jing,Yan, Ming
supporting information, p. 550 - 554 (2017/01/25)
Visible-light-promoted intermolecular radical cyclization of disulfides and alkynes has been developed. Benzothiophenes bearing ester, ketone, aldehyde and aryl substituents were synthesized in good yields. The reaction was carried out in the absence of t
Iodine-catalyzed Sulfonylation of Arylacetylenic Acids and Arylacetylenes with Sodium Sulfinates: Synthesis of Arylacetylenic Sulfones
Meesin, Jatuporn,Katrun, Praewpan,Pareseecharoen, Chayaporn,Pohmakotr, Manat,Reutrakul, Vichai,Soorukram, Darunee,Kuhakarn, Chutima
, p. 2744 - 2752 (2016/04/26)
A highly efficient and generally applicable iodine-catalyzed reaction of arylacetylenic acids and arylacetylenes with sodium sulfinates for the synthesis of arylacetylenic sulfones was developed. The methodology has the advantages of a metal-free strategy, easy to handle reagents, functional group tolerance, a wide range of arylacetylenic acids and arylacetylenes, and easy access to arylacetylenic sulfones. (Chemical Equation Presented).
Oxidation of organic sulfides and disulfides with a tert-butyl hydroperoxide-aluminum tri-tert-butoxide system
Zaburdaeva,Dodonov
, p. 185 - 187 (2011/09/12)
Methyl phenylethynyl and phenyl phenylethynyl sulfides are selectively converted into methyl phenylethynyl and phenyl phenylethynyl sulfones, respectively, under the action of system tert-butyl hydroperoxide-aluminum tri-tert-butoxide in benzene at 20 °C. The analogous oxidation of diphenyl disulfide results in S-phenyl benzenethiosulfonate.
PREPARATION AND REACTIVITY OF ARYLSULFONYL SUBSTITUTED CYCLOPROPENES
Padwa, Albert,Wannamaker, M. Woods
, p. 6139 - 6156 (2007/10/02)
A study of the cycloaddition behaviuor of several arylsulfonyl substituted alkynes with 2-diazopropane has been carried out.These activated acetylenes react to give 3H-pyrazoles which extrude nitrogen on photolysis to produce cyclopropenes in high yield.Soft nucleophiles such as thiophenoxide readily add to the activated pi-bond to give thiophenyl substituted cyclopropanes.Reaction of 1-phenylsulfonyl-2,3,3-trimethylcyclopropene with n-butyllithium followed by alkylation with various electrophiles produces arylsulfonyl substituted methylene cyclopropanes.These compounds undergo thermal rearrangement to the thermodynamically more stable isopropylidene cyclopropane.
Methyl Group Migration in the Reactions of Alkynyltrialkylborates
Pelter, Andrew,Drake, Robert A.
, p. 4181 - 4184 (2007/10/02)
It is shown that the methyl group cannot be used as a cheap, non-migrating group in the reactions of alkynyltrialkylborates with electrophiles.However, trimethylborane can be used as a methylboronating agent for alkynes, given the right choice of solvent, and this may be of use in terpene synthesis.
173.Ru-Catalyzed Oxidations with Iodosylbenzene Derivatives. Substituent Effects on Selectivity in Oxidation of Sulfides and Alcohols
Mueller, Paul,Godoy, Jose
, p. 1790 - 1796 (2007/10/02)
Oxidation of sulfides witth PhIO/RuCl2(PPh3) leads to sulfones.Electronwithdrawing substituents in the aromatic ring of PhIO reduce the reactivity and improves selectivity of the system.Thus, with m-iodosylbenzoic acid sulfides are converted to sulfoxide.Under the same conditions aliphatic primary alcohols are transformed to aldehydes with m-iodosylbenzoic acid, while PhIO affords carboxylic acids.
