Tandem Nucleophilic Addition/Diels-Alder Reaction ofN-ButadienylN,O-Ketene Silyl Acetals with C60: Stereoselective Formation of Bicyclic Octahydroquinolino-1,2,3,4-Tetrahydrobuckminsterfullerenes and Combined NMR Spectroscopic and Computational Evaluation of the Functionalization Reactions

Author(s):  
Yves Rubin ◽  
Padma S. Ganapathi ◽  
Andreas Franz ◽  
Yi-Zhong An ◽  
Wenyuan Qian ◽  
...  
2018 ◽  
Vol 4 (5) ◽  
Author(s):  
Guoxiong Hua ◽  
J. Derek Woollins

Abstract Organic selenium- and tellurium-phosphorus compounds have found wide application as reagents in synthetic inorganic and organic chemistry, such as oxygen/chalcogen exchange, oxidation/reduction, nucleophilic/electrophilic substitution, nucleophilic addition, free radical addition, Diels–Alder reaction, cycloadditions, coordination, and so on. This chapter covers the main classes of phosphorus-selenium/tellurium reagents, including binary phosphorus-selenium/tellurium species, organophosphorus(III)-selenium/tellurium compounds, phosphorus(V)-selenides/tellurides, diselenophosphinates/ditellurophopshinates, diselenaphosphetane diselenides, Woollins’ reagent, phosphorus-selenium/tellurium amides, and imides. Given the huge amount of literature up to mid-2017, this overview is inevitably selective and will focus particularly on their synthesis, reactivity, and applications in synthetic and coordination chemistry.


Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 30-32
Author(s):  
Thomas V. Lee ◽  
Alistair J. Leigh ◽  
Christopher B. Chapleo

2020 ◽  
Author(s):  
Radu Talmazan ◽  
Klaus R. Liedl ◽  
Bernhard Kräutler ◽  
Maren Podewitz

We analyze the mechanism of the topochemically controlled difunctionalization of C60 and anthracene, where an anthracene molecule is transferred from one C60 monoadduct to another one under exclusive formation of equal amounts of C60 and the difficult to make antipodal C60 bisadduct. Our herein disclosed dispersion corrected DFT studies show the anthracene transfer to take place in a synchronous retro Diels-Alder/Diels-Alder reaction: an anthracene molecule dissociates from one fullerene under formation of an intermediate, while already undergoing stabilizing interactions with both neighboring fullerenes, facilitating the reaction kinetically. In the intermediate, a planar anthracene molecule is sandwiched between two neighboring fullerenes and forms equally strong "double-decker" type pi-pi stacking interactions with both of these fullerenes. Analysis with the distorsion interaction model shows that the anthracene unit of the intermediate is almost planar with minimal distorsions. This analysis sheds light on the existence of noncovalent interactions engaging both faces of a planar polyunsaturated ring and two convex fullerene surfaces in an unprecedented 'inverted sandwich' structure. Hence, it sheds light on new strategies to design functional fullerene based materials.<br>


2016 ◽  
Vol 20 (22) ◽  
pp. 2421-2442 ◽  
Author(s):  
Kévin Cottet ◽  
Maria Kolympadi ◽  
Dean Markovic ◽  
Marie-Christine Lallemand

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