scholarly journals MS 4A-Promoted Aqueous Phospho-Aldol-Brook Rearrangement Reaction of Isatins

Heterocycles ◽  
2022 ◽  
Vol 104 (1) ◽  
pp. 159
Author(s):  
Takeshi Oriyama ◽  
Wei Han ◽  
Fan Liu
Keyword(s):  
Brook Rearrangement ◽  
Rearrangement Reaction

scholarly journals DBU Catalyzed Phospho-Aldol-Brook Rearrangement for Rapid Preparation of α-Phosphates Amide in Solvent-Free Conditions

Catalysts ◽  
2020 ◽  
Vol 10 (12) ◽  
pp. 1445
Author(s):  
Shunhong Chen ◽  
Shengxin Guo ◽  
Feng He ◽  
Yingxia Zhang ◽  
Zengxue Wu ◽  
...  
Keyword(s):  
Room Temperature ◽  
Solvent Free ◽  
The Novel ◽  
Rapid Preparation ◽  
Good Tolerance ◽  
Amide Derivatives ◽  
Solvent Free Conditions ◽  
Brook Rearrangement ◽  
Rearrangement Reaction ◽  
Dialkyl Phosphites

The 1,8-diazabicyclo [5.4.0] undec-7-ene DBU-catalyzed Phospho-Aldol-Brook Rearrangement reaction of α-ketoamide and dialkyl phosphites was developed under solvent-free at room temperature. The novel α-Phosphate Amide derivatives could be obtained with good yield (86–96%), which also exhibited good tolerance of various dialkyl phosphites and α-ketoamide, including isatins. In addition, the reaction was conducted in both gram-scale and mol-scale, and the title compounds could also be obtained in excellent yield (more than 91%) within 5 min.

scholarly journals Organic Base Catalyzed Cascade Phospho-Aldol-Brook Rearrangement Reaction of Isatins with H-phosphonates

2014 ◽  
Vol 34 (6) ◽  
pp. 1177 ◽  
Author(s):  
Wei Fang ◽  
Guogui Liu ◽  
Xiaofei Huang ◽  
Jun Jia ◽  
Xingwang Wang
Keyword(s):  
Organic Base ◽  
Brook Rearrangement ◽  
Rearrangement Reaction

scholarly journals Research Progress in [1,2]-Phospha-Brook Rearrangement Reaction

Daxue Huaxue ◽  
2020 ◽  
Vol 0 (0) ◽  
pp. 1-0
Author(s):  
Xiyuan Zhang ◽  
Yuming Li ◽  
Zhiwei Miao
Keyword(s):  
Research Progress ◽  
Brook Rearrangement ◽  
Rearrangement Reaction

Mechanistic investigation on N → Cα → O relay via non-Brook rearrangement: reaction conditions promote synthesis of furo[3,2-c]pyridinones

2017 ◽  
Vol 15 (43) ◽  
pp. 9127-9138 ◽  
Author(s):  
Lihan Zhu ◽  
Haiyan Yuan ◽  
Jingping Zhang
Keyword(s):  
Dft Calculations ◽  
Reaction Conditions ◽  
Mechanistic Investigation ◽  
Brook Rearrangement ◽  
Rearrangement Reaction

DFT calculations disclosed the effect of reaction conditions on the effective anion relay sequence of a NaH promoted non-Brook rearrangement.

Synthesis, Structure and Reactivities of Pentacoordinated Phosphorus–Boron Bonded Compounds

2020 ◽  
Author(s):  
Nathan O'Brien ◽  
Naokazu Kano ◽  
Nizam Havare ◽  
Ryohei Uematsu ◽  
Romain Ramozzi ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Ring Expansion ◽  
Bicyclic Compound ◽  
Compound A ◽  
Ligand System ◽  
Large Bulk ◽  
Rearrangement Reaction ◽  
Hydride Abstraction ◽  
Pentacoordinated Phosphorus ◽  
Acids And Bases

<div>The isolation and reactivities of two pentacoordinated phosphorus–tetracoordinated boron bonded compounds were</div><div>explored. A strong Lewis acidic boron reagent and electron-withdrawing ligand system were required to form the</div><div>pentacoordinated phosphorus state of the P–B bond. The first compound, a phosphoranyl-trihydroborate, gave a THF</div><div>stabilised phosphoranyl-borane intermediate upon a single hydride abstraction in THF. This compound could undergo a</div><div>unique rearrangement reaction, that involved a two-fold ring expansion, to give an unusual fused bicyclic compound or it</div><div>could act as a mono-hydroboration reagent. The hydroboration reactivity of the intermediate was found to be more reactive</div><div>towards alkynes over alkenes with good to moderate regioselectivity towards the terminal carbon. The second compound,</div><div>a phosphoranyl-triarylborate, was found to have a vastly different reactivity to the trihydroborate as it was highly stable</div><div>towards acids and bases. This is thought to be due to the large bulk around the P–B bond as shown in the crystal structure</div>

scholarly journals Oxidative cyclo-rearrangement of helicenes into chiral nanographenes

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Chengshuo Shen ◽  
Guoli Zhang ◽  
Yongle Ding ◽  
Na Yang ◽  
Fuwei Gan ◽  
...  
Keyword(s):  
Functional Materials ◽  
Optical Devices ◽  
Oxidative Cyclization ◽  
Synthetic Chemistry ◽  
Aromatic Rings ◽  
Cyclization Reactions ◽  
Rearrangement Reaction ◽  
Skeletal Reconstruction ◽  
Gradual Release

AbstractNanographenes are emerging as a distinctive class of functional materials for electronic and optical devices. It is of remarkable significance to enrich the precise synthetic chemistry for these molecules. Herein, we develop a facile strategy to recompose helicenes into chiral nanographenes through a unique oxidative cyclo-rearrangement reaction. Helicenes with 7~9 ortho-fused aromatic rings are firstly oxidized and cyclized, and subsequently rearranged into nanographenes with an unsymmetrical helicoid shape through sequential 1,2-migrations. Such skeletal reconstruction is virtually driven by the gradual release of the strain of the highly distorted helicene skeleton. Importantly, the chirality of the helicene precursor can be integrally inherited by the resulting nanographene. Thus, a series of chiral nanographenes are prepared from a variety of carbohelicenes and heterohelicenes. Moreover, such cyclo-rearrangement reaction can be sequentially or simultaneously associated with conventional oxidative cyclization reactions to ulteriorly enrich the geometry diversity of nanographenes, aiming at innovative properties.

Facile pinacol coupling of aliphatic ketones by Brook rearrangement in the presence of samarium species

2021 ◽  
pp. 153069
Author(s):  
Xincan Wang ◽  
Guanqun Xie ◽  
Yanfei Zhao ◽  
Ke Zheng ◽  
Yanxiong Fang ◽  
...  
Keyword(s):  
Aliphatic Ketones ◽  
Pinacol Coupling ◽  
Brook Rearrangement

Catalyst-Free [2,3]-Sigmatropic Rearrangement Reactions of Photochemically Generated Ammonium Ylides

Synthesis ◽  
2019 ◽  
Vol 51 (23) ◽  
pp. 4348-4358 ◽  
Author(s):  
Fang Li ◽  
Feifei He ◽  
Rene M. Koenigs
Keyword(s):  
Visible Light ◽  
Sigmatropic Rearrangement ◽  
Tertiary Amines ◽  
Amino Esters ◽  
Catalyst Free ◽  
Rearrangement Reaction ◽  
Rearrangement Reactions ◽  
Free Ammonium

The rearrangement reaction of ammonium ylides furnishes valuable α,α-disubstituted amino esters. In this work, we describe the visible-light photolysis reaction of aryldiazoacetates in the presence of tertiary amines that react via a free ammonium ylide in a sigmatropic rearrangement reaction to provide amino esters in moderate to very good yields (33 examples, up to 97% yield).

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