Extension of carbon chains by. gamma.-alkylation of metalated. alpha.,. beta.-ynamines

EJ Corey, DE Cane

Index: Corey,E.J.; Cane,D.E. Journal of Organic Chemistry, 1970 , vol. 35, p. 3405 - 3409

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Citation Number: 31

Abstract

Results The first ynamine we chose to study was l-diethylaminopropyne (2). This substance underwent metalation with n-butyllithium-tetramethylethylenediamine complex as evidenced by subsequent reaction with trimethylchlorosilane, which gave the acetylenic silane 3 in 85% yield (vpc analysis), Using identical conditions, however, reaction of this metalation product of 2 with either methyl iodide or allyl bromide gave neither of the expected ...