Synthesis of bicyclic diones and thiones. Facile methylation of the enolates of bicyclo [2.2. 1] heptane-2, 5-dione and bicyclo [2.2. 2] octane-2, 5-dione. An AM1 …

…, S Yeroushalmi, H Guan-Lin

Index: Werstiuk, N. H.; Yeroushalmi, S.; Guan-Lin, Hong Canadian Journal of Chemistry, 1992 , vol. 70, # 3 p. 974 - 980

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Citation Number: 15

Abstract

A group of bicyclic ketones and thiones have been synthesized for homenolization studies. Bicyclo [2.2. 1] heptane-2, 5-dione (6) undergoes unusually rapid tetramethylation giving 3, 3, 6, 6-tetramethylbicyclo [2.2. 1] heptane-2, 5-dione (1) in good yield. Treatment of 1 with P2S5 in xylene gave 3, 3, 6, 6-tetramethylbicyclo [2.2. 1] heptane-2, 5-dithione (2) and 3, 3, 6, 6-tetramethyl 15-oxo-bicyclo [2.2. 1] heptane-2-thione (3), which was converted into 4 ...