Photochemical rearrangement reactions of bicyclic molecules that contain a cyclopropane ring

2018 ◽  
Vol 42 (14) ◽  
pp. 11438-11449 ◽  
Author(s):  
Shih-Hao Su ◽  
Ming-Der Su
Keyword(s):  
Cyclopropane Ring ◽  
Quantum Yields ◽  
Photochemical Rearrangement ◽  
Rearrangement Reactions ◽  
Bicyclic Molecules

Our theoretical observations indicate that for [2.1.0], [3.1.0], [4.1.0], and [5.1.0] molecules, the quantum yields of the tautomeric keto forms are larger than those of the corresponding enol isomers.

Photochemical Rearrangement Reactions of 2-n-Propylcyclopentanone

1965 ◽  
Vol 69 (9) ◽  
pp. 3145-3147 ◽  
Author(s):  
R. Srinivasan ◽  
Sheldon E. Cremer
Keyword(s):  
Photochemical Rearrangement ◽  
Rearrangement Reactions

Interaction of heterocycles and nucleophiles. II. Sigma complexes formed from methoxide ion and Methoxy-3,5-dinitropyridines in dimethyl sulphoxide

1970 ◽  
Vol 23 (5) ◽  
pp. 957 ◽  
Author(s):  
MEC Biffin ◽  
J Miller ◽  
AG Moritz ◽  
DB Paul
Keyword(s):  
Dimethyl Sulphoxide ◽  
No Conversion ◽  
Solvation Effects ◽  
Sigma Complexes ◽  
Sigma Complex ◽  
Methoxide Ion ◽  
Rearrangement Reactions

Contrasting behaviour is observed when 2- and 4-methoxy-3,5-dinitropyridine interact with methoxide ion in dimethyl sulphoxide. The 4-methoxy compound affords both methine and acetal sigma complexes, the latter being thermodynamically more stable. The interconversion is catalysed by methanol. Labelling experiments have established that the sigma complex from the 2-methoxypyridine is formed by addition at C6; no conversion into the acetal could be effected. These observations are rationalized in terms of differential steric and solvation effects. Demethylation and rearrangement reactions of 4-methoxy-3,5-dinitropyridine are reported.

scholarly journals Recent development and applications of semipinacol rearrangement reactions

2021 ◽  
Author(s):  
Xiao-Ming Zhang ◽  
Bao-Sheng Li ◽  
Shao-Hua Wang ◽  
Kun Zhang ◽  
Fu-Min Zhang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Quaternary Carbon ◽  
Carbon Formation ◽  
Semipinacol Rearrangement ◽  
Rearrangement Reactions

The recent development of semipinacol rearrangement is reviewed, highlighting its application in β-functionalized ketone synthesis, quaternary carbon formation and total synthesis.

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).

Photochemical Rearrangement of Oxaziridines and Nitrones in the Hexahydroindole Series: A Convenient Synthetic Route to 1-Azabicyclo[5.2.0]nonan-2-ones as Novel RGD Mimetics

2001 ◽  
Vol 3 (20) ◽  
pp. 3067-3070 ◽  
Author(s):  
Erika Bourguet ◽  
Jean-Louis Baneres ◽  
Jean-Pierre Girard ◽  
Joseph Parello ◽  
Jean-Pierre Vidal ◽  
...  
Keyword(s):  
Synthetic Route ◽  
Photochemical Rearrangement

On the mechanism of the photochemical rearrangement of 3-phenyl substituted cyclopropenes to indenes

1977 ◽  
Vol 18 (33) ◽  
pp. 2847-2850 ◽  
Author(s):  
Albert Padwa ◽  
Roman Loza ◽  
Daniel Getman
Keyword(s):  
Photochemical Rearrangement
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