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The nmr (multiplet at 7.26, ArH, singlet at 3.78, N-Cf/2-, multiplets at 1.80-2.30, CHCH2, doublet at 0.90, CH(C//3)2), infrared (KBr disk, strong absorptions at 2970, 1600, 760, and 690 cm-1), and ultraviolet (Xmax 257.5 µ (e 23,400), X shoulder 268 µ (e 21,100)) spectra were consistent with a 1-substituted 4,5-diphenylimidazole dimer, assigned the structure l,2-di(2-isobutyl-4,5diphenylimidazoyl)ethane ( 24). The mass spectrum (Table II) at 70 ev was consistent with the structure assigned.

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2-Bromo-l-butanol, 2-chloro-2-methylpropanol and 2-chloro-2-phenylethanol have been reduced to the corresponding alcohols 1-butanol, 2-methyl-1-propanol and 2-phenylethanol with lithium aluminum hydride in ether solution. This strengthens the assumption made in previous papers in this series that the halohydrins are intermediates in the reduction of the corresponding -haloacids to alcohols. Reduction of the halohydrins is facilitated by the addition of hydroxyl compounds, such as water and alcohols, to the reaction mixture. The reduction products of the above halohydrins with lithium aluminum deuteride have been investigated by mass spectrometry and infrared analysis. 2-Bromo-l-butanol is reduced normally to l-butanol-2-d. 2-Chloro-2-methylpropanol, however, gives 85% 2-methyl-l-propanol-l-d, the product of a hydride shift, and only 15% of 2-methyl-l-propanol-2-d. With 2-chloro-2-phenylethanol the product is largely (ca. 95%) 2-phenylethanol-2-d with a small amount of 2-phenylethanol-l-d. The results with the aliphatic products have been confirmed by oxidative degradation.

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