Isopropyl chloride, *H NMR

The NMR spectrum of isopropyl chloride (Figure 13 17) illustrates the appearance of an isopropyl group The signal for the six equivalent methyl protons at 8 1 5 is split into a doublet by the proton of the H—C—Cl unit In turn the H—C—Cl proton signal at 8 4 2 IS split into a septet by the six methyl protons A doublet-septet pattern is char acteristic of an isopropyl group... 

MHz H NMR spectrum of isopropyl chloride showing the doublet-septet pattern of an isopropyl group... 

The temperature dependence of the H-nmr spectrum of the isopropyl cation [38] prepared from isopropyl chloride in SOjClF-SbFg solution (Saunders and Hagen, 1968b) demonstrated rapid interchange of the two types of protons. Band shape analysis showed the reaction to be intramolecular and the activation energy to be 16.4 0.4 kcal mol-. It was suggested that the rearrangement involves n-propyl cation [39] as an intermediate (33) and that... 

Improved procedures have been described, involving the addition of nitrosyl chloride in liquid sulfur dioxide4, or the use of ethyl nitrite and sulfuric acid in ethanol/water40, but the physical constants of the product were not reported. By using sodium nitrite and hydrochloric acid in isopropyl alcohol/water at <10 C the crude product was obtained in high yield (80%)41. The H-NMR spectrum in another report indicated that the crude product, similarly prepared in 40-52% yield, was a mixture of diastereomers in an unspecified ratio30. 

Obtained from sodium-liquid ammonia reduction of 4,6-dimethoxy-l-naphthyl isopropyl ketone in THF/EtOH mixture in presence of excess ammonium chloride [7851]. b.p. 140° [7851] H NMR [7851], IR [7851]. 

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