Dehydration of alcohols derived from 1-t-butyl-3-dimethylaminopropan-1-one; a novel cleavage reaction involving 2,6-dichlorobenzylmagnesium bromide

1970 ◽  
Vol 48 (6) ◽  
pp. 1011-1013 ◽  
Author(s):  
A. F. Casy ◽  
R. R. Ison
Keyword(s):  
Magnetic Resonance ◽  
Spectroscopic Data ◽  
Proton Magnetic Resonance ◽  
Tertiary Alcohol ◽  
Cleavage Reaction ◽  
Butyl Group ◽  
Acid Catalyzed ◽  
Cis And Trans

The acid-catalyzed dehydration of 1-t-butyl-3-dimethylamino-1-phenylpropan-1-ol gives cis(t-Bu/H)1-t-butyl-3-dimethylamino-1-phenylprop-1-ene exclusively. Dehydration of the product of reaction between 1-t-butyl-3-dimetnylammopropari-1-one and 2,6-dichlorobenzylmagnesium bromide gives cis and trans 2-t-butyl-1-2,6-dichlorophenyl-4-dimethylaminobut-2-ene plus the cis aminopropene of the first reaction. The formation of the aminopropene, together with that of its precursor tertiary alcohol, represents a novel cleavage reaction of 2,6-dichlorobenzylmagnesium bromide. The configurations of the aminoalkenes were established from proton magnetic resonance spectroscopic data, the cis(t-Bu/H)but-2-ene providing a further example of a magnetically non-equivalent t-butyl group.

Studies of stereochemical influences upon anti-histaminic activity. The synthesis, configuration, and anti-histaminic properties of some isomeric aminobutenes

1969 ◽  
Vol 47 (3) ◽  
pp. 423-427 ◽  
Author(s):  
A. F. Casy ◽  
A. P. Parulkar
Keyword(s):  
Double Bond ◽  
Magnetic Resonance ◽  
Spectroscopic Data ◽  
Proton Magnetic Resonance ◽  
Acid Catalyzed ◽  
Related Compounds

The acid-catalyzed dehydration of 4-dimethylamino-2-p-methoxyphenyl-1-phenylbutan-2-ol yields all four possible 4-amino-1,2-diarylbutenes. Pure samples of each isomer have been isolated, double bond positions and configurations being established from proton magnetic resonance and ultraviolet spectroscopic data. A stereoselective route to cis aminobut-1-enes has been further investigated. The anti-histaminic properties of the reported butenes together with some related compounds are given and structural influences upon activity discussed.

Physicochemical properties of some new 1,5- and 5,5-alkyl-substituted barbituric acids

1970 ◽  
Vol 48 (14) ◽  
pp. 2274-2279 ◽  
Author(s):  
G. A. Neville ◽  
H. W. Avdovich ◽  
A. W. By
Keyword(s):  
Magnetic Resonance ◽  
Physicochemical Properties ◽  
Spectroscopic Data ◽  
Proton Magnetic Resonance ◽  
Hydroxy Derivative ◽  
The Novel

The synthesis of six new barbituric acids 1b, 3a, 4b, 5, and 6b, including the novel 5-hydroxy derivative 3b, is reported together with spectroscopic data (proton magnetic resonance, ultraviolet, and infrared) for these and for five related known barbiturates for which such data is lacking. An interesting occurrence of non-equivalence of the N-1 and N-3 CH2(Et) protons in 3b is discussed.

THE PROTON MAGNETIC RESONANCE SPECTRA OF CHRYSANTHEMUM ETHYL ESTER AND THE RELATED cis- AND trans-CHRYSANTHEMUMIC ACIDS

1962 ◽  
Vol 40 (5) ◽  
pp. 875-881 ◽  
Author(s):  
H. M. Hutton ◽  
T. Schaefer
Keyword(s):  
Magnetic Resonance ◽  
Ethyl Ester ◽  
Proton Magnetic Resonance ◽  
Acid Ethyl Ester ◽  
Proton Spin ◽  
Coupling Constants ◽  
Spin Coupling ◽  
Cis And Trans Isomers ◽  
Cis And Trans ◽  
Magnetic Resonance Spectra

The high-resolution proton magnetic resonance spectra of a mixture of the cis and trans isomers of chrysanthemum monocarboxylic acid ethyl ester have been studied. The cis-chrysanthemumic and trans-chrysanthemumic acids spectra were obtained to facilitate the interpretation of the complex spectra of the ester. The percentage of the trans isomer in the chrysanthemum ester was measured to be 62.0 ± 1.1%. The cyclopropane proton spin coupling constants were found to be Jcis = 8.7 c.p.s. and Jtrans = 5.4 c.p.s., in reasonable agreement with Karplus' calculations of the dependence of coupling constants on the dihedral angle.

Conformational analysis of coordination compounds. VI. P.M.R. study of diamagnetic five-membered diamine chelate rings

1976 ◽  
Vol 29 (1) ◽  
pp. 33 ◽  
Author(s):  
CJ Hawkins ◽  
RM Peachey
Keyword(s):  
Magnetic Resonance ◽  
Conformational Analysis ◽  
Coordination Compounds ◽  
Proton Magnetic Resonance ◽  
Equatorial Orientation ◽  
Coupling Constant ◽  
Butyl Group ◽  
Magnetic Resonance Spectra ◽  
Chelate Rings

The proton magnetic resonance spectra of a number of coba1t(111), molybdenum(0), chromium(0), platinum(11) and palladium(11) complexes of (R)-propane-1,2-diamine, (S)-3,3-dimethylbutane-1,2- diamine, (RS)-N,N,N',N?-tetramethylpropane-1,2-dime and ethane-1,2-diamine have been analysed and the coupling constant data utilized to calculate the conformational populations for the various complexes. Necessary parameters for the conformational analysis were obtained from a study of tetracyano{(S)-3,3-dimethylbutane-1,2-diamine)cobaltate(111),in which the t-butyl group was assumed to be exclusively in the equatorial orientation. The preparation and resolution of this t-butyl substituted ethane-1,2-diamine are described.

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