The methylation of some phenols and alcohols with sodium hydride / methyl iodide in tetrahydrofuran at room temperature

1973 ◽  
Vol 14 (1) ◽  
pp. 21-24 ◽  
Author(s):  
Barbara A. Stoochnoff ◽  
N.Leo Benoiton
Keyword(s):  
Methyl Iodide ◽  
Room Temperature ◽  
Sodium Hydride

N-Methylamino acids in peptide synthesis. V. The synthesis of N-tert-butyloxycarbonyl, N-methylamino acids by N-methylation

1977 ◽  
Vol 55 (5) ◽  
pp. 906-910 ◽  
Author(s):  
S. T. Cheung ◽  
N. Leo Benoiton
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Methyl Iodide ◽  
Peptide Synthesis ◽  
Room Temperature ◽  
Sodium Hydride ◽  
Amino Acid Derivatives ◽  
Enantiomerically Pure ◽  
Neutral Amino Acids ◽  
Related Data

The preparation of enantiomerically pure N-tert-butyloxycarbonyl,N-methylamino acids by N-methylation of the parent amino acid derivatives using sodium hydride and methyl iodide in tetrahydrofuran at room temperature is described for neutral amino acids including O-benzyl-protected threonine and tyrosine. Methylation of the O-benzylserine derivative under these conditions gives the N-methyldehydroalanine derivative. The β-elimination is completely suppressed, giving the corresponding N-methylserine derivative when the reaction is carried out at 5 °C. Other related data on N-methylation and N-methylamino acid derivatives are presented.

Sulfur Linkage in Vulcanized Rubber. Reaction of Methyl Iodide with Sulfur Compounds

1949 ◽  
Vol 22 (1) ◽  
pp. 1-7
Author(s):  
M. L. Selker
Keyword(s):  
Methyl Iodide ◽  
Room Temperature ◽  
Sulfur Compounds ◽  
Point Of View ◽  
Secondary Reaction ◽  
Reaction Products ◽  
Sulfide Sulfur ◽  
Vulcanized Rubber ◽  
Allyl Sulfide

Abstract The work described here is an extension of the study of the reaction of methyl iodide with sulfur compounds originally begun with the purpose of using such data in determining the sulfur linkage in vulcanized rubber. A previous paper dealt with the reactions of methyl iodide with propanethiol, propyl sulfide, propyl disulfide, allyl sulfide, and thiophene. This article adds to the list, n-butyl methallyl sulfide, allyl disulfide, allyl tetrasulfide, n-propyl tetrasulfide, and trithiane. The removal of combined sulfur from vulcanized rubber as trimethylsulfonium iodide on treatment with methyl iodide at room temperature was persuasive evidence of the presence of sulfide sulfur linked to allylic type residues. The evidence offered, however, did not constitute exclusive proof because it was not known whether still other types of sulfur linkage would also yield trimethylsulfonium iodide. To shed more light on this question, the sulfur linkages most likely to occur in vulcanizates—the allyl-alkyl monosulfide, diallyl and dialkyl di- and polysulfide—were investigated. The trithiane reaction is of interest mostly from the point of view of the reaction of overcured stocks or secondary reaction products stemming from the original polysulfides. The reactions were carried out using the method described in a previous paper.

N-Methylamino acids in peptide synthesis. VII. Studies on the enantiomeric purity of N-methylamino acids prepared by various procedures

1977 ◽  
Vol 55 (5) ◽  
pp. 916-921 ◽  
Author(s):  
S. T. Cheung ◽  
N. Leo Benoiton
Keyword(s):  
Amino Acid ◽  
Methyl Iodide ◽  
Peptide Synthesis ◽  
Liquid Ammonia ◽  
Silver Oxide ◽  
Sodium Hydride ◽  
Enantiomeric Purity ◽  
Amino Acid Analyzer ◽  
Pure Compounds ◽  
Optically Pure

The enantiomeric purity of N-methylamino acids and their derivatives obtained by various procedures has been examined by analysis with an amino-acid analyzer of the diastereomeric lysyl dipeptides formed by coupling them with a lysyl derivative. N-Benzyloxycarbonyl, and N-tert-butyloxycarbonyl,N-methylamino acids obtained by methylation of the parent derivative using sodium hydride and methyl iodide, and N-methylamino acids obtained by methylation of the p-toluenesulfonylamino acid followed by treatment with sodium in liquid ammonia, are optically pure. Compounds obtained by other procedures which include reductive alkylations or the use of silver oxide – methyl iodide are generally not optically pure.

Local mode assignments for the CD-stretching overtone spectra of deuterated methyl iodide and deuterated methyl cyanide: effects of increased interoscillator coupling on local mode states of C3v symmetry

1988 ◽  
Vol 66 (4) ◽  
pp. 628-632
Author(s):  
M. Khalique Ahmed ◽  
Bryan R. Henry
Keyword(s):  
Liquid Phase ◽  
Methyl Iodide ◽  
Room Temperature ◽  
Local Mode ◽  
Methyl Cyanide

The overtone spectra of CD3I and CD3CN are measured at room temperature in the liquid phase in the regions of CD-stretching local mode overtones corresponding to ΔvCD = 2–5. The spectra are analyzed in terms of a harmonically coupled local mode model. The local mode parameters ω, ωx, and γ′v, the interoscillator coupling between the methyl CD bonds, are determined. A comparison of the spectra of the CH3Z molecules (Z = Cl, Br, I, CN) to the spectra of CD3I and CD3CN reveals the spectral effects of increased interoscillator coupling between the CD bonds.

scholarly journals Oxygen broadening and shift coefficients in the ν6 band of methyl iodide (12CH3I) at room temperature

2019 ◽  
Vol 239 ◽  
pp. 106679 ◽  
Author(s):  
Y. Attafi ◽  
S. Galalou ◽  
F. Kwabia Tchana ◽  
J. Vander Auwera ◽  
A. Ben Hassen ◽  
...  
Keyword(s):  
Methyl Iodide ◽  
Room Temperature

POTASSIUM DERIVATIVES OF FLUORENE AS INTERMEDIATES IN THE PREPARATION OF C9-SUBSTITUTED FLUORENES: III. THE INFLUENCE OF SOLVENT AND METAL IN THE FORMATION OF C9-SUBSTITUTED FLUORENES FROM 9-FLUORENYL METALS

1961 ◽  
Vol 39 (4) ◽  
pp. 799-807 ◽  
Author(s):  
G. W. H. Scherf ◽  
R. K. Brown
Keyword(s):  
Methyl Iodide ◽  
Benzyl Chloride ◽  
Room Temperature ◽  
Organometallic Compounds ◽  
Lithium Compound ◽  
Hydrocarbon Solvents ◽  
Derivatives Of ◽  
Ether Solvents ◽  
Potassium Compound ◽  
Influence Of Solvent

Equimolar quantities of 9-fluorenyl-potassium, -sodium, or -lithium and alkyl or aralkyl halides at room temperature in ether solvents yielded a mixture of unchanged fluorene, C9-monosubstituted fluorene, and C9-disubstituted fluorene. The amount of disubstitution never exceeded that of unchanged fluorene, and was found to be maximum (∼35%) for the potassium compound in 1,2-dimethoxyethane, somewhat less for the sodium analogue, and small (∼5%) for the lithium compound. In hydrocarbon solvents such as hexane, 9-fluorenylpotassium gave only 7% of C9-disubstituted fluorene. The lithium compound, upon reaction with methyl iodide or ethyl iodide gave, along with unreacted fluorene, only C9-monosubstituted fluorene. But reaction of 9-fluorenyllithium with benzyl chloride in hexane gave a small quantity (∼5%) of disubstituted fluorene as well as the monosubstituted product.The results are explained in terms of (a) the solubilities of the organometallic compounds in ether and hydrocarbon solvents, (b) the polarity of the metal carbon bond, and (c) the acidity of the hydrogen on C9 of fluorene.

Convenient C-alkylation of some acyloins

1969 ◽  
Vol 47 (1) ◽  
pp. 163-164 ◽  
Author(s):  
Johan H. van de Sande ◽  
Karl R. Kopecky
Keyword(s):  
Methyl Iodide ◽  
Benzyl Chloride ◽  
Sodium Hydride

Acetoin, adipoin, and benzoin are conveniently alkylated by benzyl chloride and methyl iodide in 1,2-dimethoxyethane solution using sodium hydride as the base. Only alkylation at carbon is observed. Little or no alkylation occurs at oxygen.

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