33472-02-5Relevant academic research and scientific papers
BF3·OEt2-promoted tandem Meinwald rearrangement and nucleophilic substitution of oxiranecarbonitriles
Xu, Chuangchuang,Xu, Jiaxi
, p. 127 - 134 (2019/12/26)
Tandem Meinwald rearrangement and nucleophilic substitution of oxiranenitriles was realized. Arylacetic acid derivatives were readily synthesized from 3-aryloxirane-2-carbonitriles with amines, alcohols, or water in the presence of boron trifluoride under microwave irradiation, and the designed synthetic strategy includes introducing a cyano leaving group into arylepoxides and capturing the in situ generated toxic cyanide with boron trifluoride, making the reaction efficient, safe, and environmentally benign. The reaction occurs through an acid-promoted Meinwald rearrangement, producing arylacetyl cyanides, followed by an addition-elimination process with nitrogen or oxygen-containing nucleophilic amines, alcohols or water. The current method provides a new application of the tandem Meinwald rearrangement.
HETEROCYCLIC COMPOUNDS AS INHIBITORS OF CXCR2
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Page/Page column 29, (2009/10/21)
The present invention relates to compounds of formula (I) wherein R1, R2, X, Y and Z are as defined in the specification.
Hydroperoxides as Pseudohalides: Oxidation, Oxidative Alkylation, Acylation and Arylation of Acrylonitrile
Araneo, Silvia,Fontana, Francesca,Minisci, Francesco,Recupero, Francesco,Serri, Anna
, p. 1399 - 1400 (2007/10/02)
New general syntheses, based on free-radical oxidative alkylation, acylation and arylation of acrylonitrile, in the presence of ButO2H, are reported; the concept of the peroxy group as a pseudohalide is suggested to explain these new reactions.
On the Preparation of Acyl Cyanides from Aldehydes
Haerle, Helmut,Jochims, Johannes C.
, p. 1400 - 1412 (2007/10/02)
The O-silylated cyanohydrins 3 prepared from the aldehydes 1 with trimethylsilyl cyanide are oxidized photochemically or thermally with N-bromosuccinimide to afford the acyl cyanides 4a-n.Scope and limitations of the procedure are discussed.
Trimethylsilyl Cyanide - A Reagent for Umpolung, VIII. Derivatives of 2-(Trimethylsilyloxy)-2-propenenitrile. Syntheses and General Properties
Hertenstein, Ulrich,Huenig, Siegfried,Reichelt, Helmut,Schaller, Rainer
, p. 261 - 287 (2007/10/02)
Rather different derivatives of the new title compuond 7 were synthesized by routes A - H (Table 2 and 3).The effects of substituents and reaction routes on the E/Z ratios (NMR) is discussed.Replacement of SiMe3 in 7 by RCO- and MeSO2- yields other alkenes with donor (O - X) and acceptor groups (CN) at the same C-atom.Their opposite effects on the β-C-atom is estimated from the corresponding 1H- and 13C-NMR signals.
Synthesis of α,β-Unsaturated and Other Reactive Acyl Cyanides
Hoffmann, H. M. R.,Haase, Klaus,Ismail, Zeinhom M.,Preftitsi, Stamatia,Weber, Anette
, p. 3880 - 3885 (2007/10/02)
Reaktive aliphatische Acylcyanide (1 - 10, siehe Tab. 1) werden aus Acylchloriden, Natriumiodid und Kupfer(I)-cyanid unter verschiedenen Bedingungen dargestellt.Die Reaktion verlaeuft ueber die Acyliodide.
