ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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)