Science of Synthesis

Begtrup, M.; Rasmussen, L. K., Science of Synthesis, (2007) 31, 1781.

Electrophilic hydrazination of metalated arenes by dialkyl azodicarboxylates proceeds smoothly to give arylhydrazines ‌9‌ using aryllithium reagents,[‌120‌] arylmagnesium bromides (‌Scheme 10‌),[‌114‌] arylboronic acids,[‌121‌] or arylzinc chlorides.[‌122‌] A protocol generating the aryllithium by bromine–lithium exchange, using excess lithium base, tolerates the presence of a carboxylic acid group.[‌123‌]

‌Meeeee 88‌ M-Meeeeeeeeeeee ee Meeeeeeeeeeee Meeeeeee Meeee Me-eeee-eeeee Meeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeee eeeee eee eeeeeeeeeeee ee ee-eeee-eeeee eeeeeeeeeeeeeeee ee eee eeeeeeee ee e eeeeee(M) ee eeeeee(MM) eeeeeeee ee eeee eeeeeeeeeeeeee ‌88‌ (‌Meeeee 88‌).[‌888‌] Mee eeeeeeeee ee eeeeeeeeee eeee eee eeeeeeee ee eeee, eeeeee, eeeeeee, eee eeeee eeeeee.

‌Meeeee 88‌ M-Meeeeeeeeeeee ee Meeeeeeeeee Meeee Meeee Me-eeee-eeeee Meeeeeeeeeeeeeee eeeee Meeeee Meeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

Meeeeeeeeeee Meeeeeeee

[8-(Meeeeeeeeeeeee)eeeeee]eeeeeeeee Meeeeeeeeeeee (‌8‌, Me8 = 8-MeMM8M8); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee eee Meeeeeee eeeeeee eeeeeeee eeee 8-eeeee-8-(eeeeeeeeeeeeee)eeeeeee (8.88 e, 88 eeee) ee MMM (888 eM) eee eeeeee ee −88°M. Me-eeee-eeeee eeeeeeeeeeeeeeee (88.8 e, 88 eeee) eee eeeee. Meeee eeeeeeee eee 88 eee, MeMM (8.8 e, 88 eeee) eee eeeee. Mee eeeeeee eee eeeeee ee 88°M eee M8M (88 eM) eee Me8M (888 eM) eeee eeee eeeee. Mee eeeeeee eeeee eee eeeeee eeee eeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee ee eeee 8,8-eee(eeee-eeeeeeeeeeeeee)-8-[8-(eeeeeeeeeeeeee)eeeeee]eeeeeeeee ee e eeeeeee, eeeeee eee. Mee eee eee eeeeeeeee ee eMeMM (888 eM), 8.8 M MMe ee eeeeeee (888 eM) eee eeeee, eee eee eeeeeeeee eeeeeee eee eeeeee ee eeeeee eee 88 eee. Me eee eeee eeeeee ee ee, Me8M (888 eM) eee eeeee, eee eee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeee eeeee eeeeeee eeeeeeee; eeeee: 8.8 e (88%); ee 888–888°M (eee).

8,8-Mee(eeee-eeeeeeeeeeeeee)-8-(8-eeeeeeeeeeeee)eeeeeeeee (‌88‌, Me8 = 8-MMM8M8); Meeeeee Meeeeeeee:[‌888‌]

Me(MMe)8 (8 ee, 8.88 eeee) eee eeeee ee eee eeeeeee ee e eeeeeee eeee ee 8-eeeeeeeeeeeeeeeeeeee eeee (888 ee, 8.8 eeee) eee ee-eeee-eeeee eeeeeeeeeeeeeeee (888 ee, 8.8 eeee) ee MMM (8 eM). Meeee eeeeeeee ee ee eee 88 e eeeee M8, eee eeeeeee eee eeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 8:8) ee eeee e eeeee eeeee; eeeee: 888 ee (88%); ee 88–88°M.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 88/8, 888.