Notes - Metalation of 1-Methylbenzimidazole with n-Butyl-lithium

1958 ◽  
Vol 23 (11) ◽  
pp. 1791-1793 ◽  
Author(s):  
Peggy Alley ◽  
David Shirley
Keyword(s):  
1959 ◽  
Vol 37 (12) ◽  
pp. 1439-1446 ◽  
Author(s):  
A. C. Neish

A simplified technique was developed for carbonation of Grignard reagents or organolithium compounds, with C14O2 generated from barium carbonate. 3,4-(Dibenzyloxy)-bromobenzene was treated with n-butyl lithium in ether and then with C14O2 to give 3,4-(dibenzyloxy)-benzoic acid-carboxyl-C14. The yield was 74% based on barium carbonate. 2,6-Dichlorobenzoic acid-carboxyl-C14 (yield 77%) and 3,5-dichlorobenzoic acid-carboxyl-C14 (yield 76%) were prepared from the corresponding dichlorobromobenzenes by a similar sequence of reactions. Attempts to synthesize 2,4- and 2,5-dichlorobenzoic acids by this route gave poor yields of unidentified acids, from which the expected products could not be isolated.


1976 ◽  
Vol 31 (6) ◽  
pp. 790-794 ◽  
Author(s):  
Mathias Höfler ◽  
Heinz Hausmann ◽  
Wilhelm Saal

The reduction of the complexes C5H5Mn(CO)2L (L=P(C6H5)2Cl, P(C6H5)(Et)Cl and P(C6H5)Cl2) with Na in liquid NH3 yields the complexes C5H5Mn(CO)2L′ (L′=P(C6H5)2Na, P(C6H5)(Et)Na and P(C6H5)Na2).The reaction of these complexes with CH3J and of CpMn(CO)2PØ2Na with H2O, CH2Cl2, CCl4, J2 and CH3COCl are described. Furthermore it has been found, that n-butyl-lithium yields C5H5Mn(CO)2NMe2Li if reacted with C5H5Mn(CO)2NMe2H.


2004 ◽  
Vol 59 (3) ◽  
pp. 351-354 ◽  
Author(s):  
Frank Biesemeier ◽  
Ulrich Müller

The reaction of phenylpentazole, C6H5-cyclo-N5, with n-butyl lithium in tetrahydrofuran or in diethylether does not yield a lithium pentazolide such as Li(THF)4+N5−. Instead, a mixture of several primary products is obtained, which probably include lithium 1-n-butyl-5-phenyl-pentaazadienide, Li+[n-C4H9− N=N−N−N=N−C6H5]− and di-n-butyl-phenylhydrazide, Li+[(n-C4H9)2N−N−C6H5]−. After hydrolysis 1,1-di-n- butyl-2-phenylhydrazine, (n- C4H9)2N−NH−C6H5, is ob- tained with good yield. This compound is an oil that was characterized by NMR, mass and IR spectroscopy


The kinetics of the polymerization of styrene initiated by n-butyl lithium in hydrocarbon media has been studied under conditions where both initiation and propagation of growing chains takes place simultaneously and in the absence of a termination reaction. Under the conditions employed, the initiator is incompletely consumed at complete conversion of monomer to polymer and consequently the degree of polymerization of the polystyrene is greater than the ratio of monomer to initiator concentration. The quantitative results support the mechanism previously proposed by Worsfold & By water for this polymerization.


1976 ◽  
Vol 31 (12) ◽  
pp. 1654-1657 ◽  
Author(s):  
Ernst Luppold ◽  
Eugen Müller ◽  
Werner Winter
Keyword(s):  

2,5-Diphenyl-tellurophene (1) is metalated with the n-butyl-lithium/TMEDA complex. The reaction of the resulting lithiumorganic compound with electrophilic agents affords 1,4-substituted butadienes (2-8).


1972 ◽  
Vol 25 (12) ◽  
pp. 2671 ◽  
Author(s):  
RF Evans ◽  
KN Mewett

Steric hindrance prevented formation of tetra-t-butylpyrazine either when pivaloin was heated with ammonium acetate or when pivalil monooxime was reduced with zinc and alkali. Diminution of the steric hindrance of the t-butyl groups by masking them by incorporation into a seven-membered ring containing sulphur was of no avail. 2,5-Di-t- butylpyrazine resulted from the analogous reduction of t-butyl-glyoxal dioxime and could be converted into its N-oxide and N,N?-dioxide. t- Butyl-lithium reacted with the pyrazine and the mono-N-oxide to give a mixture of products including 2,3,5-tri-t-butylpyrazine whose spectroscopic properties suggested a buckling of the pyrazine ring. Benzonitrile and diphenylacetylene reacted independently in the presence of iron pentacarbonyl and gave, inter alia, 2,4,6-triphenyl- 1,3,5-triazine and hexaphenylbenzene respectively. ��� The most prominent features of the low resolution mass spectra of these pyrazines and some of their precursors are discussed and rationalized.


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