0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content. Variation 2: Using Primary or Secondary Amines

DOI: 10.1055/sos-SD-031-01728

Scholz, U.; Schlummer, B.Science of Synthesis, (2007311591.

Older procedures describe the replacement of bromine atoms with p-toluidine using strongly basic conditions, such as in the synthesis of N,N-di-4-tolylbenzene-1,3-diamine (65) from 1,4-dibromobenzene and p-toluidine (Scheme 70).[‌146‌] The shift in the substitution pattern of the central arene in the product 65 is an indication that this reaction proceeds via an aryne mechanism.

Meeeee 88 Meeeeeeee ee M,M-Me-8-eeeeeeeeeeee-8,8-eeeeeee eeee 8,8-Meeeeeeeeeeeee eee e-Meeeeeeee[‌888‌]

Meeeeeeee, eeeeee eee eeeee eeeeeeee eeeee eeeeeeeee, eeeeee eeeeee eeeee eeee eeee(eeeeeeeeeeeee)eeeeeeeee[‌888‌] ee eeeeee eeeee eee eeeeee eeee-eeeeeeee,[‌888‌] eeeeee eee eee eeeeeeeee ee M,M-eeeeeeeeeeeeee (88) eeee eeeeeeeeeeee eeeeeee eee eeeeeeeee ee eeeee e eeeeeeeeee-eeeee eeeeeeee (Meeeee 88).

Meeeee 88 Meeeeeeee ee M,M-Meeeeeeeeeeeee eeee Meeeeeeeeeee eee Meeeeeeeeeee[‌888‌]

Meeeeee, ee eee eeee eeeeeeeeee eee e eeee eeee eeee eeeeee eeeee eeeee eeeeeeeeee eeeeeeeeeeee eeeeeeeeeee eee eeeeeeeeeee ee eeeeeee eeeee ee eeeeeee eeeeee ee eeee eeeeeeeeeeee. Mee eeeee eeeeeeee eeeeeee eeeeee eee eeeeeeeee ee eeeeeeeeeeeeee, eeee ee ee eee eeeeeeeee ee 8-[(8-eeeeeeeeeee)eeeee]eeeeeee eeee (88) eeee eeeeeeeeeee eeee eee 8-eeeee-8-eeeeeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee 8-[(8-Meeeeeeeeee)eeeee]eeeeeee Meee eeee Meeeeeeeeee Meee eee 8-Meeee-8-eeeeeeeeeeee[‌888‌]

Meee eeeeeeee eeee eeeee eeee eeee-eeeeeeeee eeeeeeeeeee, eeee ee eeeeeeeeeeee. Meeee eeeeee eeeee ee eeeeeeeee eeeee eeeeeee eeeee eeee eeee eeee eeeeeee eeeeeeeeee. Meee eeeeeeee eeee eeeeeeeee eeeeeeeee, eee eeeee ee eeee eeeeeeee eee ee eeeeeee eeeeeeee. M,M-Meeeeeeeeeeeeeeeeee, eee eeeeeee, eee ee eeeee ee eeeeeeeee eeeeeee eee eeeeeeeeeee eee eeeeeeeeeee ee eee eeeeeee eeee ee 8-eeeee-8,8-eeeeeeeeeeeeeee ee eeeee M-eeeee-8,8-eeeeeeeeeeeeeee (88) (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee M-Meeee-8,8-eeeeeeeeeeeeeee eeee 8-Meeee-8,8-eeeeeeeeeeeeeee eee Meeeeeeeee[‌888‌]

Meeeeeeee-eeeeeeeee eeeeeeeeeee ee e eeeeeee eeee eeee eeeeeee eeeeee ee ee eeeeeeeee eeeeeee eeeeeeee ee eeeeeeeeee.[‌88‌‌888‌] Meee eeeeee ee eee eeeeeeeeee, eeeee eeee ee ee ee eeeeeeeeeee eee eeee eeeeeeee eeee eee eeeeeeeee eeeeeeeeee eeee eeee eeeeeeeee, eeeeeee eeee eeee eeee eeeeeeeeee, e.e. eeee eeeee eee eee eeeeeeeeeeee, ee eeeeeeee eeee eeeeeee eeeeeeeeee eee eeeeeeeeee eeeeeeeee eeee eeeeeeeee eeeeeeeeeeee.[‌888‌]

Meeeee eeeeeeeee eeeeee eee ee eeeeeeee ee e eeeeeeeeeeeeeee eeeeeee eeeee eeeeeeeee eeee-eeeeeeee ee eee eeee, eeee(eeeeeeeeeeeeeeeeeeee)eeeeeeeeeee(8) ee eee eeeeeeeee eeeeee, eee eee eeeeeeeee 8,8-eee(eeeeeeeeeeeeeeeee)-8,8-eeeeeeeeee ee eee eeeeee ee eeeeeee ee 88°M ee eeeee, eee eeeeeee, 8-(8,8-eeeeeeeeeeeeee)-8-eeeeeeeeeeeeeeee (88) eeee 8-eeeeeeeeeeeeeeee eee 8-eeeee-8,8-eeeeeeeeeeeeeee (Meeeee 88).[‌888‌,‌888‌]

Meeeee 88 Meeeeeeee ee 8-(8,8-Meeeeeeeeeeeee)-8-eeeeeeeeeeeeeeee eeee 8-Meeeeeeeeeeeeeee eee 8-Meeee-8,8-eeeeeeeeeeeeeee[‌888‌,‌888‌]

Meeeeee, eeeee eeeeeeeee eeeeeee eeeeeee eeeeeee eee eeeeeeeee eeeeee eeeeeee, ee eee eeeeeee ee eee eeeeee eeeeeeeee eeeeeeeee ee eeeeeeeeee eeee 8-eeeeeeeeeeee ee eeeee 8-(8-eeeee)eeeeeeeeee (88) (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee 8-(8-Meeee)eeeeeeeeee eeee Meeeeeeeee eee 8-Meeeeeeeeeee[‌888‌]

Meeeeee eeeeeeeee eeeeee eeee eeeee ee eeee eeeeeeee eeeeeeeee eee eeeeeeeee-eeeeeeeee eeeeeeee eeeeeeeee. M-Meeeeeeeeeee eee 8-eeeee-8,8-eeeeeeeeeeeeeee, eee eeeeeee, eeeee M-eeeee-8,8-eeeeeeee-M-eeeeeeeeeeeee (88) eeeee e eeeeeeeeeeeeeeeeeeeeeeeeeee eeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee M-Meeee-8,8-eeeeeeee-M-eeeeeeeeeeeee eeee M-Meeeeeeeeeee eee 8-Meeee-8,8-eeeeeeeeeeeeeee[‌888‌]

Meeeeeeee, eeeeeeeee eeeeee eeee eeeee eeee eeeeeeeeeee eeee eeeeee eeeee eeee ee eeeeee eeeeeeeee eee eeee. Meee, 8-eeeeeeeeeeeeeeeee eee M-eeeeeeeeeeee eeeee 8-[eeeee(eeeeee)eeeee]eeeeeeeeeeee (88) (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee ee 8-[Meeee(eeeeee)eeeee]eeeeeeeeeeee eeee 8-Meeeeeeeeeeeeeeee eee M-Meeeeeeeeeee[‌888‌]

Meeeeeeeeeeeee eee eeeeeeeeeee eeeee eeeeeeeeeeeee eeee ee eeee eeeeeeeeeee eeeee e eeeeee eeee eee eeeeeee(eeeeeeee)eeeeeeeee eeeeee, ee eee eeeeeee ee eee eeeeeeeee ee 8,8-eeeeeeee-M,M-eeeeeeeeeeeeeee (88) eeee 8-eeeee-8,8-eeeeeeeeeeeeeee eee eeeeeeeeeeeee (Meeeee 88).[‌888‌,‌888‌]

Meeeee 88 Meeeeeeee ee 8,8-Meeeeeee-M,M-eeeeeeeeeeeeeee eeee 8-Meeee-8,8-eeeeeeeeeeeeeee eee Meeeeeeeeeeee[‌888‌,‌888‌]

Meeeeee eeeeeeeee eeeeee eeee eeeee ee eeeeeeeee eeeeeeeeeeee ee eeeeeeeee-eeeeeeeee eeeeeeee eeeeeeeeee. Meeeeeeeee eeeeeeeeeee ee eee eee ee eeee eeeee eeee ee eeeeeeeee eeeeeeeee ee eeeeee eeeeeeeee. Meee eeeeeeee eee eeee eeeeeeee ee eee eeeeeeeee ee eeeeee 8-(eeeeeeeeee)eeeeeeee (88) eeee eeeeee 8-eeeeeeeeeeeee eee eeeeeeeeee (Meeeee 88).[‌888‌,‌888‌]

Meeeee 88 Meeeeeeee ee Meeeee 8-(Meeeeeeeee)eeeeeeee eeee Meeeee 8-Meeeeeeeeeeee eee Meeeeeeeee[‌888‌,‌888‌]

Meee eeeeeeeee eeeeeeee eeeeeeeeeee eee eee ee eeeeeeeeee, eeee ee ee eee eeeeeeeee ee M-eeeee-8,8-eeeeeeeeeeeeeee (88) eeee 8-eeeee-8,8-eeeeeeeeeeeeeee eee eeeeeeeeee (Meeeee 88).[‌888‌,‌888‌]

Meeeee 88 Meeeeeeee ee M-Meeee-8,8-eeeeeeeeeeeeeee eeee 8-Meeee-8,8-eeeeeeeeeeeeeee eee Meeeeeeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeee 8-(Meeeeeeeee)eeeeeeee (88); Meeeeee Meeeeeeee:[‌888‌,‌888‌]

Me eeee-eeeee Meeeeee eeeee eee eeeeeee eeee Me8MM8 (888ee, 8.8eeee) eeee eee eeee eeeeee eeeeee eeee e eeeeee eee eeeeee. Mee eeeee eee eeeeee eeee e eeeeee eeeeee eee eeee eeeeeee eeee Me8(eee)8 (88ee, 8.88eeee) eee MMMMM (88ee, 8.88eeee), eee eeeeee eeee eeeee. Meeeee 8-eeeeeeeeeeeee (888ee, 8eeee), eeeeeeeeee (888ee, 8.8eeee), eee eeeeeee (8eM) eeee eeeee, eee eee eeeeeee eee eeeeee ee 888°M, eeee eeeeeeee, eee 88e. Mee eeeeeee eee eeeeee ee ee, eeeeeee eeee Me8M (88eM), eeeeeeee, eee eeeeeeeeeeee. Mee eeeee eeeeeee eee eeee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee); eeeee: 888ee (88%).