Science of Synthesis

Witulski, B.; Alayrac, C., Science of Synthesis, (2006) 24, 1009.

A general route to N,N-bis(trimethylsilyl)alky-1-yn-1-amines ‌13‌ is based upon the reactions of lithium acetylides ‌11‌ with O-(2,4,6-trimethylbenzenesulfonyl)-N,N-bis(trimethylsilyl)hydroxylamine (‌12‌) (‌Scheme 3‌).[‌28‌] By contrast, the electrophilic amination of the acetylides ‌11‌ cannot be performed with O-methanesulfonyl- or with O-diphenylphosphinyl-N,N-dimethylhydroxylamine. However, such reactions readily proceed with dilithium trialk-1-ynylcuprates ‌14‌, which are generated in situ from the corresponding lithium acetylides ‌11‌, to afford N,N-dimethylalk-1-yn-1-amines ‌15‌ (‌Scheme 3‌).[‌29‌]

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M,M-Mee(eeeeeeeeeeeeee)-8-eeeeeeeeeeeeee-8-eeeee (‌88‌, M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

Mee eeeeeeeeeeeee ‌88‌ (8.88 e, 88 eeee) ee Me8M (888 eM) eee eeeee ee eeeeeee eeeeeeeeeeeeeee (88 eeee) [eeeeeeee ee eeeeeeee eeeeeeeeeeeeeee (8.88 e, 88 eeee) eeee 8.8 M MeMe (88 eeee) ee eeeeee (8.88 eM)] ee eeeee Me8M (88 eM) ee −88°M eee eeeeeeeee eeeee eeeee. Mee eeeeeee eee eeeeeee ee ee eee 88 e. M eeeeeeeeeee eeee eee eeeeee eee eeeeeee ee eeeeeeeeee, eee eee eeeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeee eeeeeeeee eeeeeee e Meeeeee eeeeee (88 ee), eeeeee e eeeeeeeee eeeeee; eeeee: 8.88 e (88%); ee 88°M/8.88 Meee; MM ν̃ 8888 (M≡M) ee−8.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) M 88-8, 8888.
• 8.Meeeee-Meee, (8888) M 88-8, 8888.
• 8.Meeeee-Meee, (8888) M 88-8, 8888.