Science of Synthesis

Lawrence, S. A., Science of Synthesis, (2009) 40, 566.

As alkylating agents, sulfonates are in many instances superior to halides (see Section ‌40.1.1.5.4.3‌), because sulfonates are often better leaving groups. If primary amines such as butylamine are reacted with 1 equivalent of a sulfonate, either one or both hydrogen atoms attached to nitrogen can be displaced resulting in mixtures of secondary amines ‌181‌ and tertiary amines ‌182‌ (‌Scheme 110‌).[‌328‌] The choice of solvent, as well as the ratio of amine to sulfonate can affect the product distribution (see Houben–Weyl, Vol. 11/1, p 217).[‌329‌]

‌Meeeee 888‌ Mee Meeeeeee ee Meeeeee Meeeee eeee Meeeeeeeee[‌888‌]

Mee eeeeeeee ee eee(eeeeeeee)-eeeeeeeeeee eeeeeee eeee eeeeeee eeeeee eeeee ee eeeeee eeeeeeee eeeeee, e.e. ‌888‌,[‌888‌,‌888‌] eee eee eeeeee ee eeee eeeeee eeeeee eeee eee(eeeeeeee)-eeeeeeeeeee eeeee eeeeee eeee 8-eeeeeeeeeeeee eee eeeeee eeee eee eeeeeeeeeeeee eeeeeeee eeee eeeeeeeeeeeee eee eeee eeeee eeee eeeeeeee (‌Meeeee 888‌).[‌888‌]

‌Meeeee 888‌ Meeeeeeee ee Meeeee Meeeee ee Meeeeeeeeeee ee Meeeeeeeee[‌888‌,‌888‌]

‌Meeeeeeeeee 888M‌

‌Meeeeeeeeee 888M‌

Meeeeeee eee(eeeeeeeeeee)eeeeeee ‌888‌ eeeee eeee eeeeeeeee eeeeee ee eeee eeeeeeeeeeeee eeeeeeeeeeeee eeeeeeee ‌888‌ eeee e eeeeee eeeee eeeee.[‌888‌] Mee eeeeeeee eeee eeeee eee eeeeeeeeeee eee(eeeeeeeeee) (eeeeee eeeeeeee eeeeeeee) eee eee eee(eeeeeeeeee) eeeeeeeeee eeeee eeeeeeeeeeeeeee. Me eeeeeee eeeeee eee eeeeeee eeee eee[8-(eeeeeeeeeee)eeeee] eeeeee, 8-eeeeeeeeeee eeeeeeeeeee ‌888‌ eee eeeeeeee (‌Meeeee 888‌).[‌888‌]

‌Meeeee 888‌ Meeeeeeee ee Meeeee Meeeeeee eee Meeeeeeeeee eeee Mee(eeeeeeeeee)[‌888‌]

‌Meeeeeeeeee 888‌

Meeeeeeee ee 8-(eeeeeeeeeeee)eeeeeee eeee 8-eeeeeeeeeeeeeee eeeeeeee eeeeeeee ee eeeeeeeee eeeeeeeee eeeee 8,8-eeeeeeeeeeeeeeeee eeeeeeeeeeeee (‌888‌) eee eee eeeeeeeeeeeee eeeeeeeeeeeeeeeeee eeee ‌888‌ (‌Meeeee 888‌).[‌888‌]

‌Meeeee 888‌ Mee Meeeeeeee ee 8,8-Meeeeeeeeeeeeeeee Meeee 8-Meeeeeeeeeeeeeeee[‌888‌]

Mee eeeeeeeeeee eeeeeeeee 8,8,8,88,88,88-eeeeeeeeeeeeeeeeeeeeee (‌888‌) eee ee eeeeeeeeeee ee e eeeeeee eeeeeeeee (‌Meeeee 888‌).[‌888‌]

‌Meeeee 888‌ Meeeeeeee ee e Meeeeeeeee Meeee ee Meeeeeeeeeee ee Meeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeee Meeeeeee Meeeee ‌888‌; Meeeeee Meeeeeeee:[‌888‌]

Mee eeeeeee eeeee (8.8 eee) eee eeeee eeeeeeee eeee 8 e ee e eeee ee eee eee(eeeeeeeee) ee eeeee eeeeeee (888 eM). MeMM (88 e, 8.8 eee) ee M8M eee eeeee eee eee eeeeee ee eee eeeeeee eee eeeeeee ee eee-eeee ee eeeeeeeeeeee. Mee eeeeeee eee eeeeee, Me8M eee eeeee, eee eee eeeeeee eee eeeeeeee eee eeee eeeeeeeee. Meeeeeeeeeeeee eeee eee eeeeee eeeeeeee eeeee.

M,M,M′,M′-Meeeeeeeeeeeeeee Meeeeeee ‌888‌; Meeeeee Meeeeeeee:[‌888‌]

Mee eee(eeeeeeeee) ‌888‌ eee eeeeeeee eeee eee eeeee eeeeeeeee eeeee (88 eeeee) eeeee eeeeeeeee eeeeeeeeee eee 88 e. Meeeee eeeee eee eeeeeee ee eeeeeeeeee eeeeeeeeeeee eee eeee eeeeee 88% ee MeMM eee eeeee ee eee eeeeeee. Mee eeee eeeee eee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M. Mee Me8M eeeee eee eee eeeeeee eeee eeeee eeee eeeeeeee eee eeeee (M8MM8), eee Me8M eee eeeeeee ee eeeeeeeeeeee. Mee eeeeeeee eee eee eeeeeeee ee eeeeeeeeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee.

8,8-Meeeeeeeeeeeeeeee Meeeeeeeeeeeeee (‌888‌); Meeeeee Meeeeeeee:[‌888‌]

MeMe (88 e, 888 eeee) eee eeeee Me8MM8 (88 e, 888 eeee) eeee eeeee ee eeeee eeeeeee (888 eM) (MMMMMMM: eeeeeeeeee) eee eee eeeeeee eee eeeeeee eeeeee eee eeeeeeee ee 8-(eeeeeeeeeeee)eeeeeee (88 e, 888 eeee) ee eeeeeee (88 eM). Mee eeeeeee eee eeeeeeee ee e eeeee eeee eee e eeeeeee 8 e. Meee eeeeeee, e eeeeeeeeeee eeee eeeeeeeeeeee, eeeee eee eeeeeeeee ee eeeeeeeeee. Mee eeeee eee eeeeee eeee eeeeeee eee Me8M eee eeee eeeee. Mee eeeeeeee eeee eeeeeeeee eeee MeMM (888 eM) eee 8 e ee eeee 8,8,8,8-eeeeeeeeeeeeeeeeeeeeee eee(8-eeeeeeeeeeeeeeee) (‌888‌); eeeee: 88 e (88%).

8,8,8,8-Meeeeeeeeeeeeeeeeeeeee eee(8-eeeeeeeeeeeeeeee) (‌888‌; 88.8 e, 88 eeee) eee eeeeeeeee ee 88% MeMM (888 eM) ee eeeeee eee 88% MMM (8.8 e, 88 eeee) ee MeMM (888 eM) eee eeeee. Mee eeeeeee eee eeeeeee eee e eee e. Meeee eeeeeee, MeMM eeeeeeeeeeee eee eee eeeeeee ee eeeeeeeeee. Meeeeeee ee eeeee MMe ee eee eeeeeeee ee eeeeeeee eeeeeeee ee MMe(e) eee 8–88 eee eeeeeee eee eeeeeeee eeeeeeee ee eeeeeee ee eee MeMM ee eeeeeeeeeeee eeee e eeeee eeee. MeMM eee eeeee ee eeee eeeeeee eee eeee eeeeeee eeeee eeeeeee eeeeeeee. Meee eeeeeee eee eeeeeeee 8–8 eeeee, eeeee eeeee 8,8-eeeeeeeeeeeeeeeee eeeeeeeeeeeeeee eee eeeeeeee ee e eeeeeeeeeee eeeeee, eeeee eee eeeeeeeeeeeeee eeee MeMM; eeeee: 8 e (88%).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 88/8, 888.
• 8.Meeeee-Meee, (8888) 88/8, 888.
• 8.Meeeee-Meee, (8888) M 88e8, 888.