22396-75-4Relevant academic research and scientific papers
Grignard Addition Reactions to 1,4-Difunctionalized But-2-ynes
Silva, Anthony N. De,Francis, Craig L.,Ward, A. David
, p. 1657 - 1672 (2007/10/02)
Trisubstituted alkenes of E geometry have been prepared by anti addition of Grignard reagents to 1,4-difunctionalized but-2-ynes.Addition of primary, secondary and aromatic Grignard reagents to but-2-yne-1,4-diol provided (E)-2-substituted but-2-ene-1,4-diols as major products along with the corresponding 2-substituted buta-2,3-dien-1-ols.Addition of phenylmagnesium bromide to the mono- and di-methyl ethers of but-2-yne-1,4-diol gave 2,3-diphenyl-1,3-diene.Treatment of 4-dimethylaminobut-2-yn-1-ol with primary alkyl and alkenyl Grignard reagents afforded the 2-substituted anti addition product regiospecifically, stereospecifically and in high yield.Reaction of 1-dimethylamino-4-methoxybut-2-yne with butylmagnesium bromide provided only the 3-substituted anti addition product in good yield.
A quick procedure for the preparation of 1-N,N-dialkylamino-1-buten-3-ynes
Brandsma,Verkruijsse
, p. 807 - 810 (2007/10/02)
1-N,N-Dialkylamino-1-buten-3-ynes, HC≡CCH=CHNR2 (R = CH3 or C2H5, E/Z ratio ~97:3) have been prepared in 80 and 84% yields by treating the Mannich-coupling products from HC≡CCH2OCH3 and R2NCH2OH, CH3OCH2C≡CCH2NR2, with two equivalents of potassium amide in liquid ammonia and subsequently adding methanol or ammonium chloride.
