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 ...
[Heathcock, Clayton H.; Buse, Charles T.; Kleschick, William A.; Pirrung, Michael C.; Sohn, John E.; Lampe, John Journal of Organic Chemistry, 1980 , vol. 45, # 6 p. 1066 - 1081]
