The chemistry of carbanions. 29. The nature of the enolate formed by addition of lithium dimethylcuprate to enones

HO House, JM Wilkins

Index: House,H.O.; Wilkins,J.M. Journal of Organic Chemistry, 1976 , vol. 41, # 25 p. 4031 - 4033

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Citation Number: 35

Abstract

4-Methoxy-2-methylthio-N-methylthiobenzamide(8). A solution of 1.36 g (7.5 mmol) of thioamide IC in 20 ml of dry THF was cooled in an ice bath under N2. Then 10 ml (l6 mmol) of a 1.6 m solution of n-BuLi in hexane was added dropwise and stirred for 8.5 h at room temperature. The reaction mixture was recooled in an ice bath and 800 mg (8.5 nimol) of methyl disulfide added. The mixture was stirred at 25" C for 18 h, quenched with water, ...