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Reactions of 5,5-dimethyl-1,3-cyclohexanedione anion with substituted benzyl bromides

P. Hrnčiar and K. Fabianová

Department of Organic Chemistry, Faculty of Natural Sciences, Komenský University, 801 00 Bratislava

 

Abstract:  Reactions of 5,5-dimethyl-l,3-cyclohexanedione anion with substituted X-benzyl bromides in acetone were carried out. Under the applied experimental conditions all four possible benzyl derivatives were formed except for the reactions with p-methoxybenzyl bromide. It was found that the substituent X affected the C/O ratio of the formed derivatives according to the Kornblum rule and log C/0 = f( σ+). In the reactions with m -substituted X-benzyl bromides to the second degree, a partial steric hindrance was observed on the softer carbon nucleophiHc centre.

Full paper in Portable Document Format: 304a520.pdf

 

Chemical Papers 30 (4) 520–529 (1976)

Wednesday, May 22, 2024

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