Science of Synthesis

Rademacher, P., Science of Synthesis, (2009) 40, 1199.

A general method for the preparation of (trialkylammonium)acylimines ‌230‌, starting from 1,1-dialkylhydrazines, follows the sequence acylation, alkylation, deprotonation (‌Scheme 108‌).[‌260‌–‌264‌] This method requires that alkylation occurs at the right nitrogen atom, leading to quaternization of N1 (cf. Section ‌40.7.1.1.2.2‌). This is the case with most reactive alkylation reagents; however, difficulties have been observed with 1-bromopropane[‌261‌] and 1-iodododecane.[‌256‌] Several steps can often be performed without isolating an intermediate such as the 2-acyl-1,1,1-trialkylhydrazinium salts ‌229‌. In the last step, deprotonation is effected with dilute sodium hydroxide or titration to pH 9. Products are isolated by extraction, e.g. with chloroform.

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‌Meeeeeeeeee 888‌

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‌Meeeee 888‌ Meeeeeeee ee (Meeeeeee)eeeeeeeeee eeee Meeeeeeee eeee Meeeeeee eee Meeee Meeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

(Meeeeeeeeeeeeeeee)eeeeeeeeeeeeeeeee (‌888‌, M8 = MMe=MM8; M8 = Me); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: 8,8-Meeeeeeeeeeeeeeee ee eeeeeeeee ee eeee, eeee, eee eeeeee eeeeeeeee, eeeeeee eeeeeeeee eeee eeeeeeee, eee ee e eeeeeeee eeeee eeeeeeeeee.

Me e eeeeeee eeee ee 8,8-eeeeeeeeeeeeeeeee (888 e, 8.8 eee) ee eeeeeee (8 M) (MMMMMMM: eeeeeeeeee) ee 8–88°M eee eeeee eeeeeeeeeeee eeeeeeee (888 e, 8.8 eee) eeee 8 e. Meeee eee eeeeeee eee eeeeeee ee eeee ee ee, eee eeeeeeeeeee eee eeeeeee ee eeeeeeeeee, eee eee eeeee eee eeeeeeeee eeee eeee eeeeeee (8 × 8 M). Mee eeeeeeee eeee eeeeeeee eeee eee eeeeeeee eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee M′,M′,8-eeeeeeeeeeeeeeeeeeeeeeee ee e eeeee eeeee; eeeee: 888.8 e (88%); ee 88–88°M [88°M eeeee eeeeeeeeeeeeeeeee (eeeeee)].

M′,M′,8-Meeeeeeeeeeeeeeeeeeeeeee (88.8 e, 8.888 eee) eee MeMMe (88.8 e, 8.888 eee) eeee eeeeeeee ee MeMM (888 eM) eee 8 e. Meee eee eeeeeee eee eeeeee ee ee, M′,M′,8-eee­eeee­eeeeeeeeeeeeeeeeeee 8-eeeeeeeeeeeeeeee (888, M8 = MMe=MM8; M8 = Me; M = MMe) eeeeeeeeeeee ee e eeeee eeeee. Meeeeeeeeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee eeee eeee eeeeeee; eeeee eeeee: 88.8 e (88%); ee 888–888°M.

Mee eeee 888 (M8 = MMe=MM8; M8 = Me; M = MMe; 88 e, 88 eeee) ee eeeeeeeee M8M (888 eM) eee eeeeeeeeeee eeee 88% ee MeMM (eeeeeeeee: eeeeeeeeeeeeeee). Meeeeeeeeee ee M8M eeeee eeeeeee eeeeeeee eeee e eeeee eeeee, eeeee eee eeeeeeeee eeee eeee MMMe8. Meeeeeeeeeeee ee eee eeeeeeee eeeeeeee e eeeee eeeee; eeeee: 8.8 e (888%); ee 888–888°M (eeeeeee).

(Meeeeeeeeeeeeeeee)(8-eeeeeeeeeeeeeeee)eeeee (‌888‌, M8 = Me; e = 8); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeeee, eeeeeeeee, ee eeee eeeeeeeeee ee eeeeeeeeeee eee ee eeeee.

M eeeeeee ee eeeeee-8-eee (8.8 e, 8.88 eee) eee 88% M8M8•M8M (8.8 e, 8.88 eee) eee eeeeeee ee 88°M eee 8 e. Meeee eeeeeeeeeee ee eee eeeeeeeee M8M8, MeM (88.8 e, 8.88 eee) eee eeeeeee eeee eee eeeeeeeeee ee eee eeeee 8-eeeeeeeeeeeeeeeeeeeeeee (88.8 e, ~8.8 eee) eee M8MM8 (88.8 e, 8.88 eee) ee MeMM (888 eM) ee 88°M eee eeeee. Mee eeeeeee eee eeeeeee eee 8 e ee eeeeee eeeeeeeeeee, eee eeee ee eeeeeeeee eeeee eee eeeeeeeee ee eeeeeeeeee. Meeeee MeM eee eee eeeeeee ee eee eeeeeeee eeee eeeeeee ee eeeeeeeeeee. Mee eeeeeee eee eeeeeeeee eeee eeeeeee eeeeeee eeeee, eeeeeeee ee eeeeeeeeee eee eeeeeeeeeee ee eee eeeeeee; eeeee: 88.8 e (88%). Mee eeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeeeeee (eeeeeee) ee eeee, eeeee eeeeeee; eeeee: 8.8 e (88%); ee 888–888°M.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88e8, 8888.