BF3•OEt2 Catalysed chemoselective C=C bond cleavage of α,β-enones: An unexpected synthesis of 3-alkylated oxindoles and spiroindolooxiranes

2021 ◽  
Author(s):  
Sengodagounder Muthusamy ◽  
Ammasi Prabu
Keyword(s):  
Double Bond ◽  
Boron Trifluoride ◽  
Bond Cleavage ◽  
Boron Trifluoride Etherate ◽  
Cleavage Reaction ◽  
Bond Cleavage Reaction

A BF3•OEt2 catalyzed highly chemoselective formal C=C double bond cleavage reaction of α,β-enones with diazoamides for the synthesis of 3-alkylated oxindoles is developed. Boron trifluoride etherate is found to be...

Electrocatalytic C-C Double Bond Cleavage Reaction of Styrene with Molecular Oxygen Mediated by CuCl2

1993 ◽  
Vol 22 (3) ◽  
pp. 395-398 ◽  
Author(s):  
Toshihiro Koyama ◽  
Akira Kitani ◽  
Sotaro Ito ◽  
Kazuo Sasaki
Keyword(s):  
Double Bond ◽  
Molecular Oxygen ◽  
Bond Cleavage ◽  
Cleavage Reaction ◽  
Bond Cleavage Reaction

The photochemistry of aliphatic and alicyclic α,β-unsaturated nitro compounds. A study of double bond cleavage following intramolecular cyclization and nitro-nitrite rearrangement

1984 ◽  
Vol 37 (6) ◽  
pp. 1231 ◽  
Author(s):  
RD Grant ◽  
JT Pinhey
Keyword(s):  
Double Bond ◽  
Intramolecular Cyclization ◽  
Methyl Acrylate ◽  
Room Temperature ◽  
Bond Cleavage ◽  
Nitro Compounds ◽  
Significant Extent ◽  
Cleavage Reaction ◽  
Nitrile Oxides ◽  
Bond Cleavage Reaction

The light-induced intramolecular cyclization of α, β-unsaturated nitro compounds leading to double bond cleavage, which had previously been detected in a small number of β-nitrostyrenes and α-nitro-stilbenes, has been shown to occur in a range of aliphatic and alicyclic α, β -unsaturated nitro compounds. At room temperature the reaction competes to a significant extent with the well known nitro-nitrite rearrangement in the irradiation of 1-nitro-2-phenylcyclohexene (2), 1-methyl-2-nitro-cyclohexene (6), 1-methyl-2-nitrocycloheptene (11), 2-methyl-3-nitrobut-2-ene (23) and 2-nitro-3-phenylbut-2-ene (24), while it was the only reaction detected in the case of 1-methyl-2-nitrocyclo- octene (12) and 1-nitrocyclooctene (19). No evidence for the cleavage reaction was found with 1-methyl-2-nitrocyclopentene (10), 1-nitrocyclohexene (17), 1-nitrocycloheptene (18) and 3-nitropent-2-ene (25). The nitrile oxides produced in the double bond cleavage reaction were trapped in a cycloaddition with methyl acrylate, yielding 3-substituted methyl 4,5-dihydroisoxazole-5-carboxylates. Irradiations of 1-methyl-2-nitrocyclohexene (6) and 1-methyl-2-nitrocycloheptene (11) in refluxing benzene afforded only the bridged ring isoxazolines (30) and (31) respectively. Syntheses of a number of nitro-olefins are also reported.

Double bond cleavage reaction of silyl enol ethers using MoO2(acac)2-tBuOOH

1981 ◽  
Vol 22 (27) ◽  
pp. 2595-2598 ◽  
Author(s):  
Kiyotomi Kaneda ◽  
Nobuyoshi Kii ◽  
Koichiro Jitsukawa ◽  
Shiichiro Teranishi
Keyword(s):  
Double Bond ◽  
Bond Cleavage ◽  
Cleavage Reaction ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Bond Cleavage Reaction

Nitro–Nitrite Isomerization and Transition State Switching in the Dissociation of Ionized Nitromethane: A Threshold Photoelectron–Photoion Coincidence Spectroscopy Study

2009 ◽  
Vol 15 (2) ◽  
pp. 157-166 ◽  
Author(s):  
Brandon Ferrier ◽  
Anne-Marie Boulanger ◽  
David M.P. Holland ◽  
David A. Shaw ◽  
Paul M. Mayer
Keyword(s):  
Transition State ◽  
Ab Initio Calculations ◽  
Ab Initio ◽  
Bond Cleavage ◽  
Cleavage Reaction ◽  
Nitrite Ion ◽  
Methyl Nitrite ◽  
Bond Cleavage Reaction ◽  
Entropy Of Activation ◽  
Lower Entropy

Threshold photoelectron–photoion coincidence (TPEPICO) spectroscopy has been employed to investigate the competition between bond cleavage and rearrangement reactions in the dissociation of ionized nitromethane, 1. Modeling TPEPICO breakdown diagrams with a combination of RRKM theory and ab initio calculations at the G3 level of theory allowed the derivation of the activation energy for the isomerisation of 1 to ionized methyl nitrite, 2, 82 kJ mol−1. In addition, evidence was found for a transition state switch in the bond cleavage reaction in 1 leading to CH3• + NO2+. As internal energy increases, the effective transition state for this reaction becomes tighter (i.e. is characterized by a lower entropy of activation, Δ‡S). Fitted thresholds for NO+ and CH2OHO+ ions, originating from the isomeric methyl nitrite ion, are consistent with G3 level ab initio calculations.

Biosynthesis of C11 and C16 homoterpenes in higher plants; stereochemistry of the CC-bond cleavage reaction

Tetrahedron ◽  
1998 ◽  
Vol 54 (49) ◽  
pp. 14725-14736 ◽  
Author(s):  
Wilhelm Boland ◽  
Andreas Gäbler ◽  
Matthias Gilbert ◽  
Zhuofu Feng
Keyword(s):  
Higher Plants ◽  
Bond Cleavage ◽  
Cleavage Reaction ◽  
Bond Cleavage Reaction

A novel CC bond cleavage reaction of 2, 2′-pyridil in solution

2010 ◽  
Vol 19 (11) ◽  
pp. 1116-1118
Author(s):  
Rui Ren ◽  
Pin Yang ◽  
Xiang-Lin Jin
Keyword(s):  
Bond Cleavage ◽  
Cleavage Reaction ◽  
Bond Cleavage Reaction

scholarly journals Theoretical Study of the Ti–Cl Bond Cleavage Reaction in TiCl4

2017 ◽  
Vol 231 (9) ◽  
Author(s):  
Daniel Nurkowski ◽  
Ahren W. Jasper ◽  
Jethro Akroyd ◽  
Markus Kraft
Keyword(s):  
Theoretical Study ◽  
Bond Cleavage ◽  
Cleavage Reaction ◽  
Bond Cleavage Reaction ◽  
Kinetics Of

AbstractIn this work the kinetics of the TiCl

ChemInform Abstract: Zinc-Acetic Acid Promoted Reductive Carbon-Nitrogen Bond Cleavage Reaction of α-Aminoketones.

ChemInform ◽  
2014 ◽  
Vol 45 (24) ◽  
pp. no-no
Author(s):  
Hideaki Fujii ◽  
Kyoko Ishikawa ◽  
Miyuki Tomatsu ◽  
Hiroshi Nagase
Keyword(s):  
Acetic Acid ◽  
Bond Cleavage ◽  
Cleavage Reaction ◽  
Bond Cleavage Reaction ◽  
Nitrogen Bond

Silver Nitrate Mediated Cyclization/N–N Bond-Cleavage Reaction for the Synthesis of 3-Arylisoquinolines

Synlett ◽  
2016 ◽  
Vol 27 (18) ◽  
pp. 2597-2600 ◽  
Author(s):  
Yun-Hui Zhao ◽  
Yubo Li ◽  
Mingjian Luo ◽  
Zilong Tang ◽  
Keqin Deng
Keyword(s):  
Silver Nitrate ◽  
Bond Cleavage ◽  
Cleavage Reaction ◽  
Bond Cleavage Reaction
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