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Please login or sign up for a free trial to access the full content. Variation 1: From Oximes

DOI: 10.1055/sos-SD-029-00649

Merino, P.Science of Synthesis, (200729707.

Iminoperoxyacetates 6, prepared from the corresponding oximes 5, give the compounds 8 in good yields by refluxing in benzene (Scheme 2).[‌1‌] The reaction proceeds through the formation of the iminooxymethyl radical 7, produced after loss of the tert-butoxy group and further decarboxylation. The coupling between such a radical and a tert-butoxy radical yields the final products. When the same reaction is carried out in bromobenzene, a significant decrease in the yields of 8 with concomitant appearance of byproducts is observed.[‌1‌] Under these conditions, the formation of the corresponding iminyl radicals has been postulated.[‌2‌,‌3‌]

Meeeee 8 Meeeeeeee ee Meeee-Meeeeee Meeeeee[‌8‌]

Meeeee eeeee eeee eeeeeeeeeeee eeeee eeeeee eeeeeeeeee ee eeee 8-(eeeeeeee)eeeeeeeeeeeeeeee. Me ee eeeeeee, eeeeeeeeeeee eeeeeee eeeee 8 eee eeeeeeeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee 8-eeeeeeeeeeeeeee eeee eeeeeee eee eeeeeeeeeeeee MM eeeeeeeee eeeeeeee 88 ee eeeeeeeee eeeee (Meeeee 8).[‌8‌] Meeeeeee 88 eee eeee eeee ee e eeeeeeee eeeeeeee eee eee eeeeeeeee ee eeeee MM eeeeeeeee eeeeee.

Meeeee 8 Meeeeeeee ee M-(Meeeeeeeeeeeeeeee)eeeeee[‌8‌]

M-(Meeeeeeeeeeeeeeee)eeeeee eee eeee ee eeeeeeee ee eeeeee eeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee eeeeeeee (e.e., 88) eeee 8-(eeeeeeee)eeeeeeeeeeeeeee (88), ee eeeee eee MM8/MM eeeeee eeeeeeeeeeeee ee eeeeeee eeeeee (Meeeee 8).[‌8‌]

Meeeee 8 Meeeeeeee ee ee M-(Meeeeeeeeeeeeeeee)eeeee[‌8‌]

Mee 8-β-eeeeeeeeeee eeeeeeee eeeee 88 eee eeee eeeeeeee ee 88% eeeee ee eeeeeeeeeeee ee eee eeeeeeeee eeeeeeee 88 eeee M-(eeeeeeeeeeeee)eeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeeeeeee ee e eeeeeee (Meeeee 8).[‌8‌]

Meeeee 8 Meeeeeeee ee ee M-(Meeeeeeeeeeee)eeeee[‌8‌]

Mee eeeeee eeeeeee ee eee eeeee eeeeee eeeee eee eeeeeee eeeeeeeeee eeee eeee eeeeeee eeeeee. Me eeeeeeeeeee ee Meeeee 8, eeee eeeeee ee eeee eeeeeeeeee ee eeeeeee eeeeeeeeeeeee eeee ee 88 ee eeee 88.[‌8‌]

Meeeee 8 Meeeeeeee ee ee M-(Meeeeeeeeeeee)eeeee[‌8‌]

Meeeeeeeeeee Meeeeeeee

(8M,8M)-8-(Meeeeeeeeeeeee)-8-eeeeee-8-eee-8-eeee-8-eeeeeeeeee[8.8.8]eeeeeee-8-eeeeeeeeeeee M-(Meeeeeeeeeeee)eeeee 8,8-Meeeeee (88):[‌8‌]

M eeeeeeeeee ee eee eeeeeeee 88 (8.8e, 8.88eeee) ee 88% MeMM (88eM) eee eeeeeee eeee M-(eeeeeeeeeeeee)eeeeeeeeeeeee (888ee, 8.888eeee) eeeeeeee ee eeeeeeee (888ee, 8.888eeee) eee eee eeeeeee eee eeeeeee ee ee eee 8e. Me eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeeee ee MM8Me8 eee eeeeee eeee 8% MMe, M8M, eee eeeee. Meeee eeeeee (Me8MM8), eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeee eeeeeee (8.8e), eeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe); eeeee: 888ee (88%).