(Co)cyclodimerization of alkynes by aluminum halides. Synthesis of pyridines from aluminum halide .sigma. complexes of cyclobutadienes and nitriles

1982 ◽  
Vol 47 (6) ◽  
pp. 989-997 ◽  
Author(s):  
H. Hogeveen ◽  
R. F. Kingma ◽  
D. M. Kok
2007 ◽  
Vol 1056 ◽  
Author(s):  
Andrew P Purdy ◽  
Joel B Miller ◽  
Rhonda M Stroud ◽  
Katherine A Pettigrew

ABSTRACTSolutions or mixtures of aluminum halides AlX3 (X = Cl, Br, I) or aluminum halide alkoxide (ROAlX2; R= i-Pr, X = Cl, Br) are prepared in toluene, or pentamethyldiethylenetriamine (PMDETA) and treated with a slight excess of 50:50 (wt.) sodium potassium alloy (Na/K). Upon agitation, the reaction takes place slowly. The reaction appears to be limited by the deposition of insoluble products on the surface of the Na/K since sonication in an ordinary ultrasonic cleaner is necessary to bring the reaction to completion in several hours. Aluminum nanoparticles (NPs) and Na and K halides are formed, and soluble Al compounds, are also formed in some cases. Lithium powder is used instead of Na/K to reduce Al(N(SiMe3)2)3 to Al NPs. In an effort to passivate the surface of the Al particles to oxidation or hydrolysis, various agents are added either during the reaction or afterward. The products are characterized by SEM, XRD, NMR, and TEM, and the stability to water and air is evaluated.


1970 ◽  
Vol 23 (5) ◽  
pp. 957 ◽  
Author(s):  
MEC Biffin ◽  
J Miller ◽  
AG Moritz ◽  
DB Paul

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.


2019 ◽  
Vol 25 (31) ◽  
pp. 7457-7462 ◽  
Author(s):  
Michael Mauksch ◽  
Svetlana B. Tsogoeva
Keyword(s):  

1964 ◽  
Vol 3 (5) ◽  
pp. 385-386 ◽  
Author(s):  
W. P. Neumann ◽  
R. Schick ◽  
R. Koster

ChemInform ◽  
1990 ◽  
Vol 21 (51) ◽  
Author(s):  
N. KAMIGATA ◽  
T. SUZUKI ◽  
M. YOSHIDA
Keyword(s):  

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