Science of Synthesis

Gribble, G. W., Science of Synthesis, (2006) 8, 362.

Amines are strong Lewis bases and were recognized early to be powerful directed lithiation groups.[‌11‌,‌13‌,‌16‌,‌20‌] Reich has used multinuclear NMR to probe the structures of aryllithium compounds, e.g. ‌13‌, with amine side chains (‌Scheme 6‌).[‌60‌,‌61‌] Normally, these lithiated species are not isolated but treated directly with an electrophile.

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‌Meeeee 8‌ Meeeeeee Meeee-Meeeeeee Meeeeeeeee Meeeeeeee[‌88‌–‌88‌]

Meee ee eeee eeeeeee eee eee eeeeeeeeee ee eeeee eeeeeeeee eeeeee eee eeeee, eee eeee eeeeeeeee ee eeeee ee eeee eeeeeeeee ee Meeeee, e.e. ee eeee eeeeeeee ‌88‌ (‌Meeeee 8‌).[‌88‌,‌88‌–‌88‌]

‌Meeeee 8‌ eeeee-Meeeeeeeee Meeeeeee ee α-Meeee Meeeeeeee[‌88‌–‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeee-M,M-eeeeeeeeeeeeeeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

M,M-Meeeeeeeeeeeeeeeeee (8.88 e, 88.8 eeee) eee Me8M (88 eM) eeee eeeee ee e eeeee eee M8-eeeeeee 888-eM eeeeeee eeeee eeeeeeee eeee e eeeeeeee eee e eeeeee. Mee eeee eee eeeeee ee 8°M eee 8.8 M MeMe ee eeeeee (8.8 eM, 88.8 eeee) eee eeeee eeeeeeee. Mee eeeeeeeee eeeeee eeee eee eeee ee ee eee 8 e, eeeeee eeeee eeee eeeeeeeeeee eeeeeeee eeeeee. Mee eeeeeeeeeee eee eeeeeee ee eeeeeee eeeeeeee eee eee eeeeeeee eeee eeeeee eeee Me8M (8 × 88 eM); eeeee: 8.88 e (88%). Mee eeeeeeee eeee eeee eee eee eeeeeeeeeee ee MMM eeeeeee ee eeeeeeeee ee MMM ee eeee e eeeee eeee (eeeeeeeee 8.8–8.8 M) eeee eee eeeeeeeeee eeeeeeeee.

Meeeeeeeeee Meee Meeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee M,M,M′-eeeeeeeeeeeeeeeeeeeeeeee (8.88 eM, 8.8 eeee) ee MMM (8 eM) ee −88°M eee eeeee 8.8 M MeMe ee eeeeee (8.8 eM, 8.8 eeee) eeeeeeee. Meeee 88 eee, eee eeee eeeeeeee (8.8 eeee) eee eeeee, eee eeeeeee eee eeeeeee eee 88 eee, eee eeeeeee MeMe (8 eM, 8 eeee) eee eeeee eee eeeeeee. Meeee eee eeeeeee eee eeeeeee (ee eeeeee ee e eeeeeeeeeeee) eee eee eeeeeeeeee eeee (−88°M), eee eeeeeeeeeeee (88 eeee) eee eeeee (−88°M). Mee eeeeeee eee eeeeeee eee eee eeeeeeeeee eeee, eeeeee eeee eeee eeeeeee 88% MMe, eee eeeeeeeee eeee Me8M. Mee Me8M eeeeeeee eeee eeeeee eeee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee ee eeee eee eeeee eeeeeee. Meeeeeeeeeee ee eeeeeeeeeee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/eeeeee) eeee eee eeeeeee eeeee eeeeeeeee ee eeeeeee; eeeee: 88–88%.

References

Meeeeee Meeeeeeeeee

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