Science of Synthesis

Subramanian, L. R., Science of Synthesis, (2004) 19, 118.

O-Alkyl- and O-aryl-substituted aldoximes are converted into the corresponding nitriles by milder methods than the aldoximes themselves and a few reports provide convenient syntheses of nitriles by this procedure.

Me eeeeeee eeeeeeeeee ee eeeee M-eeeeeeeeee ‌88‌ eeee eeeee-eeeeeee eeeeeee ‌88‌ eee eeee eeeeeeee ee eeeeeeee eeee 8 eee% ee Meeeee' eeeeeeee ee eeeeeee ee 88°M (‌Meeeee 88‌).[‌88‌] Meee eeeeeeeeee, eeeeeeee eeeee eeeeee ee eeeeeee e eeee-eeeeeee eeeeeeeeee eeeeeeee ee eeeee eeeeee, eee eeee eeeeeeeee eeee e eeee eeeeee eee eeeeeeeee eeeee-eeeeeeeeeee eeeeeeee. Meeeee' eeeeeeee eee eeee ee eeeeeeee ee eeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM) eee eeeeeeeeee eeee eeeeeeee ee eee eeee eeeee ee 8 eee%, eeeeeeee eeeeeeeee(MMM) eeeeeeee eeeeeeee 88 eee% eee e eeeeee eeee eee eee eeee eeeeeeee. Meeeeeeeeee eeeee-eeeeeee eeeeee eeeeeee eeee eeeeeeeeee eeee eeeeeeee eeeeeeee, eeeeeeeeee eeee eeeeeeeeee eeeeee eee eee eeeeee.[‌88‌] Me eeeeeee ee eee eeeeeeeeee ee eeeee-eeeeeee eeeee ‌88‌ eeee eeeeeee ‌88‌ ee eeeee ee ‌Meeeee 88‌. Me ee eeeeeeeee, 8-eeeeeeeeeeeeeeeeeee eeeee eee eeee eeeeeeeee eeee 8-eeeeeeeeeeeeeeeeeee, eeeeeeee ee eeeeeeeeeeeeee ee Meeeee' eeeeeee eee eeeeeeee–eeeeeee eeeeeeeeee eee eeee eeeeeee.

‌Meeeee 88‌ Meeeeeee ee e Meeee-Meeeeee M-Meeeeeeeee eeee Meeeee' Meeeeeee[‌88‌]

‌Meeeee 88‌ Meeeeeeeeee ee e Meeee-Meeeeee Meeeeee[‌88‌]

Me eeee eeeeeeeee M-eeeeeeeeeee eeeeeeeeeee eeee ee M-eeeeeeeeeeeeee eeeeeeeee ‌88‌ eee eeee eeeeeeeeee eee eeeeeeee ‌88‌.[‌88‌] Mee eeeeeeee ee eeeeeeeee ee eeeee eeeeeeee eeeeee eeeee ee eeeeee eeeeeeeeeeee eeee eee eeeeeeeee ‌88‌ ee eeee eeeeeeeeeee eeeeeeee ee eeeeeeeeee eee eeeeeeeeeee eee eeeeeeeeeeee (‌Meeeee 88‌). Mee eeeeee ee eeeeeeeee eee eeeeeeee eeeeeeee ‌88‌ eee eeee eeee, eeeeeeee eeee eeee ee eeeee ee eeeeeeeeee eee eeeeeeee eee ee eee eeeeeeeee ee eeeeeeee eeeeeee. Meee eeeeeeee ee eeeeeeeeeeee eeeeeeee eee eeeeee eeeeeeee eeeeeee eee eeeeeeee eee eeeeee ee eeeeeee eee eee ee eeeeeeee eeeeeeeee eee.

‌Meeeee 88‌ Meeeeeeeeee ee Meeeeeeee eeee Meeee Meeeeeeeeeeee[‌88‌]

Meee eeee eeeeeeeee ‌88‌ eee eeeee eeeeeeeee eeee eee eeeeeeeeeeeee eeee-eeeeeeeeeeeeeeeeee eeeeee, eeee eee ee eeeeeeee eeeeeeeeee ee eeee eeeeeeee ‌88‌ eeeee eeeeeeeee ee eeeeeeeeeeeeeeeee ee 888°M, eee e eee-eeeeeeeeeee eeeeeeeee (‌Meeeee 88‌).[‌88‌] Mee eeeeee eee eeee eeeeeeee ee eeee, eeeeeeeee eeeee 88 eeeee eee eeeeeeeeee ee eee eeeeeeee.

‌Meeeee 88‌ Meeeeeeeeee ee eeee-Meeeeeeeeeeeeeeeee Meeeee ee Meee Meeeeeeee eeee Meeeeeeee[‌88‌]

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

Mee eeeeeeee ee eee eeeee-eeeee eeeeee ee 8-eeeeeeeeeeeeeeeeeee M-eeeeeeeeee (‌88‌, M8 = Me; M8 = Me) eeeeeeeeee eee eeeeeeeeeee eeeeeeee ee eeeeeeeee eeee ee eeeeeeeee eeeeee ee eeeeee(MM) eeeeeeee eee 8 eeeeeeeeeee ee eeee eeeeee ee eeeeeeeee e-eeeeee.[‌88‌] Meee eeeeeee eeeeeeeeeee eee eeeeee, eeeeeee eeeeeeee eeee eee eeeeeeeeeeee eee eeeeeee ee eeeeee eeee eeeeee[‌88‌] eee ee eeeeeeeee ee eee eeeeeeee ee M-eeeeeeeeeee eeeeeeee ee eeeeeeeeeee ee eeee eeeeeeee eee ee eeeeeeee. Meeeeeee eee eeeeeee ‌88‌ (M8 = Me) eee eeeeee ee eee eeeeee ee 88%, eee eeeeeeee ee eee eeeeeee, eeeeeeeee ee eeeee-eeeee eeeee ee eeeeeee (‌Meeeee 88‌); eeeeeeeeeeeee eeeeeeeeeeee M-eeeeeeeeee eeee eee eeeee eeeee eeeee eeeeeeeeee. Mee eeeeeeeee ee eee eee eeeee, eee eeeeeeeeee eee eeeeeeee ee eee eeee eeeee eeeee eeeeee ee eeeeee eee eeeeeeeeeeee eeee eeeeee eee eee eeeeeeee ee eeeeeee.

‌Meeeee 88‌ Meeeee/Meee-Meeeeeee Meeeeeeee ee Meeeeeee Meeeeeee eeee Meeeeeee Meeee Meeeee[‌88‌]

Meeeeeee ‌88‌ eee eeeeeee eeeeeeee eeee eee eeeeeeeeeeeee M-eeeeee ee M-(8-eeeeeeeeeee) eeeeeeeee ‌88‌ eeee eeeeeeeee(MM) eeeeeeee ee eeeeeeeeeeee ee eeeeeee eee e Meeeeeee eeeeeeeeeeeee (‌Meeeee 88‌).[‌88‌] Meee eeeeee eee eeeeee eeee eeeeeeeeee eee eee eeeeeeeeeee ee 8-eee-8M-8-eeeeeeeeee-8-eeeeeeeeeeee eeee eee eeeeeeeeeeeee eeeee eeeeeeeeee ee e eeee eeeee ee 88% (ee. eeeee eee eee eeeeeeeeeee ee 8-eee-8M-8-eeeeeeeeee-8-eeeeeeeeeeeee eeee M-eeeeeeeeeeee).

‌Meeeee 88‌ Meeeeeeee ee Meeeeeee eeee M-Meee Meeeeeeee eeee Meeeeeeee(MM) Meeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-M-Meeee-8,8-M-eeeeeeeeeeeeee-α-M-eeeeeeeeeeeeeeeeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

Mee eeeee ‌88‌ (8.88 eeee) eee eeeeeeeee ee eeeeeee (88 eM) (MMMMMMM: eeeeeeeeee) ee e 88-eM eeeee-eeeeeeee eeeee eeeeeeee eeee e eeeeeeee eeeeeee eee, eeeeee eeeeeeeee, eee M8 eeeee. Meee, eee eeeeeeeee eeeeeeee [MeMe8(MMMe)(MMe8)8] ee MeMe8(MMe8) (8 eee%) eee eeeee. Mee eeeeeee eee eeeeee ee 88°M eee 88–88 e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeee eee; eeeee: 88–88%.

Meeeeeee ‌88‌ eeee Meeeeeeee ‌88‌ ee Meeeeeee eeee Meeee Meeeeeeeeeeee; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeee eeeeeee ee eeeeeeeee eeeeee eeee eeeeeeee. Meeeeeee eeeeeee eee ee eeeeeeee eeeeeee eee eeee eee ee eeeeeeeee eeeee.

Me e eeee ee eeeeeeee ‌88‌ (8.88 eee) ee eee MeMM eeeeeeeeee Me8M (8 eeeee) eee eeeee eeeeeeee, eeee eeeeeeee, eeeeee eeeeeeeeeeee (8.88 e, 8.88 eee) ee eeeee eeeeeeeeeeee (8.88 e, 8.88 eee) ee ee. Mee eeeeeee eee eeeeeee eee 8.8–8.8 e ee ee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee (888 Meee) eee eee eeeee eeeeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeee; eeeee: 88–88%.

8-Meeeeeeeeeeeeeeeeee (‌88‌, M8 = 8-MeMM8M8); Meeeeee Meeeeeeee:[‌88‌]

Me e eeeeeee eeee ee MeMM8 (8 eM) eeeeeeeeee 8-eeeeeeeeeeeeeeeeeee M-(8-eeeeeeeeeee)eeeee (‌88‌, M8 = 8-MeMM8M8; M8 = MM; 888 ee, 8.888 eeee) eee eeeee MeMe8 (888 ee, 8.888 eeee). Meeee eeeeeeeee eee eeeeeee eee 8 eee, M8M (88 eM) eee eeeee eeee eeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee (88 eM), eeeee (Me8MM8), eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeeee [eeeeee eee, eeeeeee (MMMMMMM: eeeeeeeeee)/MeMMe 88:8] ee eeee eee eeeeeee; eeeee: 88 ee (88%). Meeeeee eeeeeee eeee eee eeee eeeeeee eeeeeeee eee eeeee eeeeeeeeeeeee eeeeeee, 8-eeeeeeeeeeeeeeeeeee; eeeee: 88 ee (88%).

References

Meeeeee Meeeeeeeeee

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