Science of Synthesis

Mitra, S.; Gurrala, S. R.; Coleman, R. S., Science of Synthesis, (2007) 20, 1562.

Prabhakar et al. found that aroyl cyanides, when compared to aroyl chlorides, react exclusively on the oxygen atom of N-arylhydroxylamines or sterically bulky N-alkylhydroxylamines to give O-aroylhydroxylamines ‌23‌ (‌Scheme 11‌).[‌23‌] Variation of the electronic character of the substituents in the aroyl cyanide does not have any effect on the nature of the product formed. However, with electron-releasing substituents on the N-arylhydroxylamine the products obtained are the 2-hydroxy-4-methylbenzanilide (46%), 4,4′-dimethylazoxybenzene (18%), and 4-methylbenzanilide (10%).

‌Meeeee 88‌ Meeeeeeee ee M-Meeeeeeeeeeeeeeeeee eeee M-Meeee- eee M-Meeeeeeeeeeeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

Me eeeeeeeeeee eeeeee eee eee eeeeeeeee ee M-eeeeeeeeeeeeeeeeeee ee eeeeeeee eee eeeeeeeee eeeeeeeeee ‌88‌ eeee eeeee eeeeeeeee, eeeeeeeee eee eeeee eeeeee eeeeeeeeeeeee eeeeeeeee eeeeeeeee ‌88‌ (‌Meeeee 88‌).[‌88‌] Meeee eee eeee eeeeeeeee ee eeeeee eee M-eeeeeeeeeeeeeeeeeee ‌88‌.

‌Meeeee 88‌ Meeeeeeee ee M-Meeeeeeeeeeeeeeeeee[‌88‌]

M eeeeeee ee eeeeeee eeeeee eee eeeeeeeee eeee eeeee eeeeeeeeeeeee M-eeeeeeeeeeeeeeeeeeeee ‌88‌ eeeee eeeeeeee eeeeeeeeee, ee eeeeeeeee eeeeee (‌Meeeee 88‌).[‌88‌,‌88‌]

‌Meeeee 88‌ Meeeeeeee ee M-Meeeeeeeeeeeeeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeeee Meeeeeeee

M-Meee- ee M-Meeee-M-eeeeeeeeeeeeeeeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

Meeeeeee ee eeeeeeeeee eeeee eeeeeeeee eeeeeeeeeeeeee (8 eeeee) eeee eeeeeeee eeee eee eeeee eeeeeee (8.8 eeeee) ee ee eeeeeee eeeeeee [eeeeeee (MMMMMMM: eeeeeeeeee), eeeeeee, ee MM8Me8] eeeee eeeeeee eeeeeeeeee ee ee. Mee eeeeeee eeeeeeee eee eeeeeeee ee e eeeeeeeee eeee eeeee ee eeeeeeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee; eeeee: 8–88%.

M-Meeeeeeeeeeeeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

M,M-Mee(eeeeeeeeeeeeee)eeeeeeeeeeeee (88 eeee) ee Me8M (88 eM) eee eeeeeee eeee e 8.8 M eeee ee MeMe ee Me8M (88 eM, 88.8 eeee) ee −88°M eee eee eeeeeee eee eeeeeee ee ee eee 88 eee. Me eee eeeeee ee –88°M; e eeee ee eee eeeee eeeeeeee (88 eeee) ee Me8M (88 eM) eee eeeee eee eee eeeeeee eee eeeeeee eee 8 e ee −88°M eeeee eee eeee eeeeee eeeee. Meeee eeeeeeee ee eeeeeeeee eeeee (888 eM) eee eeeeeee eee eeeeee eeee M8M, eee eee eeeeeee eeeee eee eeeee (MeMM8) eee eeeeeeeeeeee ee eeeeee eee eeeeeeeeeeee eeeee eeeeeeeeee ‌88‌ ee e eeeeeeeee eee; eeeee: eee eeeeeeee.

M eeee ee ‌88‌ (88 eeee) ee MeMM (88 eM) eee eeeeeee eeee 8 M MMe (88 eM) eee eeeeeee eee (88 e). Meeee 8 eee, eee eeeeeeeee eeeee eeeeeeeeeee eee eeeeeee ee eeeeeeeeee eee eee eeeeeee eeee ee eeeeeeeeee MMe, eeeee eeeeeeee ee e eeeee eeeee; eeeee: 88% (M8 = MMe); eeeee: 88% (M8 = M).

M-Meeeeeeeeeeeeeeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

M eeee ee MMMM (8 eeeee) ee MM8Me8 (8 eM·eeee−8 ee MMMM) eee eeeee ee e eeeeeee ee eee eeeee (8 eeeee) ee e eM 88.8 eeeeeee eeeeee eeee (8 eM·eeee−8 ee eeeee) ee ee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeee ee eee eeeeeee eeee MM8Me8 eeeeeee eeeee. Mee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8), eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee; eeeee: 88–88%.

References

Meeeeee Meeeeeeeeee

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