Synthesis of tadpole polymers via triple click reactions: Copper-catalyzed azide-alkyne cycloaddition, diels-alder, and nitroxide radical coupling reactions

2012 ◽  
Vol 50 (10) ◽  
pp. 1917-1925 ◽  
Author(s):  
Tuba Dedeoglu ◽  
Hakan Durmaz ◽  
Gurkan Hizal ◽  
Umit Tunca
2020 ◽  
Vol 58 (5) ◽  
pp. 645-653 ◽  
Author(s):  
Clémence Nicolas ◽  
Wenhao Zhang ◽  
Émilie Choppé ◽  
Laurent Fontaine ◽  
Véronique Montembault

2010 ◽  
Vol 48 (10) ◽  
pp. 2214-2223 ◽  
Author(s):  
Jakov Kulis ◽  
Craig A. Bell ◽  
Aaron S. Micallef ◽  
Michael J. Monteiro

2015 ◽  
Vol 53 (20) ◽  
pp. 2381-2389 ◽  
Author(s):  
Lale Nur Atici ◽  
Erhan Demirel ◽  
Umit Tunca ◽  
Gurkan Hizal ◽  
Hakan Durmaz

1995 ◽  
Vol 73 (10) ◽  
pp. 1675-1694 ◽  
Author(s):  
Dennis G. Hall ◽  
Renate Müller ◽  
Pierre Deslongchamps

The transannular Diels–Alder reaction of 15-membered macrocyclic trienes with a trans-trans-cis (TTC) olefin geometry can lead to A.B.C.[6.6.7] tricyclic products of trans-syn-trans (TST) and cis-syn-cis (CSC) stereochemistry whereas the TTT isomers can produce the trans-anti-cis (TAC) and cis-anti-trans (CAT) tricycles. In order to study the influence of the position (pro-6.6 or pro-6.7) and the nature (alkyl, alkoxymethyl, or formyl) of the dienophile substituent, a set of 10 model cyclopentadecatrienes was prepared. The synthesis of appropriately functionalized trisubstituted dienophile and diene synthons, as well as their coupling reactions affording acyclic precursors, is described in this paper (first in a series of two). A mild and efficient macrocyclization protocol yielded the required methyl- or alkoxymethyl-substituted cyclic substrates. Further transformations led to the formyl-substituted ones. In particular, the TTT macrocycles containing an enal as a dienophile could be completely isomerized to the corresponding TTC thermodynamic isomers in acidic aqueous media. Keywords: transannular, Diels–Alder, 15-membered ring, A.B.C.[6.6.7] tricycles, diterpene.


Synlett ◽  
2017 ◽  
Vol 28 (16) ◽  
pp. 2153-2156 ◽  
Author(s):  
Wen-Ting Wei ◽  
Hongze Liang ◽  
Wen-Ming Zhu ◽  
Weida Liang ◽  
Yi Wu ◽  
...  

A radical–radical cross-coupling reaction of phenols with tert-butyl nitrite has been developed with the use of water as an additive. This method allows the construction of C–N bonds under an air atmosphere at room temperature, providing the ortho-nitrated phenol derivative in moderate to good yields.


2020 ◽  
Author(s):  
Masatoshi Kawashima

Correlation between yield and reduced mass of raw materials in intramolecular C-N, C-C, C-O coupling reactions and intramolecular/intermolecular Diels-Alder reactions was revealed. The regression equation was found to be the same as that of intermolecular reactions; yield = -0.1861<i>M</i><sub>AB</sub>/(<i>n</i><sub>A</sub><i>n</i><sub>B</sub><i>n</i><sub>I</sub>)+100.0, where <i>M</i><sub>AB</sub> is the reduced mass per mole and <i>n</i><sub>A</sub> and <i>n</i><sub>B</sub> are the total number of each reaction site in molecular A and molecular B in the reaction system, and <i>n</i><sub>I</sub> is the number to distinguish whether it is a intramolecular reaction or intermolecular reaction.


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