ChemInform Abstract: A CONVENIENT METHOD OF THE SYNTHESIS OF PHOSPHOPEPTIDE VIA AZIRIDINE RING OPENING REACTION

1980 ◽  
Vol 11 (11) ◽  
Author(s):  
K. OKAWA ◽  
Y. YUKI ◽  
T. TANAKA
Keyword(s):  
Convenient Method ◽  
Ring Opening ◽  
Aziridine Ring ◽  
Ring Opening Reaction

scholarly journals A CONVENIENT METHOD OF THE SYNTHESIS OF PHOSPHOPEPTIDE VIA AZIRIDINE RING OPENING REACTION

1979 ◽  
Vol 8 (9) ◽  
pp. 1085-1086 ◽  
Author(s):  
Kenji Okawa ◽  
Masanori Yuki ◽  
Takumi Tanaka
Keyword(s):  
Convenient Method ◽  
Ring Opening ◽  
Aziridine Ring ◽  
Ring Opening Reaction

Ring Opening of 1,1’-sulfonyl bis-aziridines Derived from L-Amino Acids and DFT Study on their Affinity Toward Different Nucleophiles

2021 ◽  
Vol 18 ◽  
Author(s):  
Nawel Khettache ◽  
Mohamed Dehamchia ◽  
Sihem Hessainia ◽  
Tahar Abbaz ◽  
Zine Régaïnia
Keyword(s):  
Ring Opening ◽  
Density Functional ◽  
Theoretical Study ◽  
Sodium Ethoxide ◽  
Aziridine Ring ◽  
Functional Theory ◽  
Cyanide Anion ◽  
Anionic Nucleophiles ◽  
Ring Opening Reaction ◽  
Selective Ring Opening

: We describe herein the ring-opening reaction of chiral 1,1’-sulfonyl bis-aziridines with various neutral and anionic nucleophiles, including benzylamine, piperidine, acetate, allyl thiolate, cyanide anion, and sodium ethoxide. These reactions afforded bis-opened or/and mono-opened compounds via a regioselective attack on the non-substituted methylene of aziridine ring. The structures of the products were confirmed based on spectral analysis (IR, 1H NMR, and 13C NMR). A theoretical study involving density functional theory (DFT) was used to rationalize the region-selective ring-opening of starting bis-aziridines.

On the Conrotatory Ring Opening of 3-Carbomethoxycyclobutene Vis-À-Vis 3-Carbomethoxy-1,2-Benzocyclobutene and the Predominant Inward Opening of 3-Dimethylaminocarbonyl-1,2-Benzocyclobutene

2018 ◽  
Author(s):  
Veejendra Yadav ◽  
Dasari L V K Prasad ◽  
Arpita Yadav ◽  
Maddali L N Rao
Keyword(s):  
Transition State ◽  
Ring Opening ◽  
Electron Process ◽  
Ring Opening Reaction ◽  
Stable Species ◽  
Electron Event

<p>The torquoselectivity of conrotatory ring opening of 3-carbomethoxycyclobutene is controlled by p<sub>C1C2</sub>→s*<sub>C3C4</sub> and s<sub>C3C4</sub>→p*<sub>CO</sub> interactions in the transition state in a 4-electron process as opposed to only s<sub>C3C4</sub>→p*<sub>CO</sub> interaction in an apparently 8-electron event in 3-carbomethoxy-1,2-benzocyclobutene. The ring opening of 3-carbomethoxy-1,2-benzocyclobutene is sufficiently endothermic. We therefore argue that the reverse ring closing reaction is faster than the forward ring opening reaction and, thus, it establishes an equilibrium between the two and subsequently allows formation of the more stable species <i>via</i> outward ring opening reaction. Application of this argument to 3-dimethylaminocarbonyl-1,2-benzocyclobutene explains the predominantly observed inward opening.</p>

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