You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via19.5.4.3 Method 3: From Organomagnesium Compounds
Please login to access the full content or check if you have access via
Subramanian, L. R., Science of Synthesis, (2004) 19, 165.
It has been proven that 2-pyridyl cyanate (10) is an appreciably good nitrile transfer reagent for organomagnesium compounds.[14] This reagent is prepared by reaction of 2-hydroxypyridine (9) with cyanogen bromide in the presence of pyridine in dichloromethane at 0°C in 90% yield (Scheme 4). The selective cyanation of a variety of Grignard reagents 11 with cyanate 10 to aryl nitriles 12 proceeds smoothly and in high yield.[14] Byproducts such as the corresponding ketone are not formed and the one apparent byproduct, 2-hydroxypyridine (9), is soluble in water making for easy isolation of the product nitriles. A number of aliphatic, aromatic, and alkynyl Grignard reagents are converted into nitriles by this method (Scheme 4).
Meeeee 8 Meeeeeeeeee ee 8-Meeeeee Meeeeee eee Mee Meeeeeeeee Meeeeeee eeee Meeeeeee Meeeeeee[88]
Meee eee eeeeeee eeeeeeeeeeeeee eeeeeeeeeeeeeee eeeeeeeee, e.e. 88, eeeee eee eeeeeee eeeeeeee ee eee eeeeeeeeeee eeeeee–eeeeeeeee eeeeeeee eeee eeeeeeeeeeeeee eeeeeee eee eeeeeeeeeee eeeeeee, e.e. 88, eeeee eeeeeeeeeeeeeeeeee eeeeeee (ee eeeeeeeeeeeeeeeeeeee),[88] eeee eeee eeee eeeeeee eeee eeeee eeeeeee (8) ee eeee eeeeeeeeeeeeee eeeeeeee, e.e. 88 (Meeeee 8).[88,88]
Meeeee 8 Meeeeeeeeee ee Meeeeeeeeeeeee Meeeeee Meeeeeee eeee Meeeeeeeeeeeeee Meeeeeee ee Meeeeeee eeee Meeee Meeeeee[88,88]
Meeeeeeee, eee eeeeee eeeeeeeeee 88 ee eeeeeeeeeee eeee eeeeeee 88 (Meeeee 8).[88,88] Meeeeeeee eeeeeeeeeeeeeeeee ee ee eeee ee e eeeee eeeee eee eeee eeee eeeeeee eee ee eeeeeeeeeeeeeee eeeeeeeee.[88]
Meeeee 8 Meeeeeeeeee eee Meeeeeee ee e Meeeeeeeeee Meeeee Meeeeeeeee eeee Meeee Meeeeee[88,88]
Meeeeeeeeeee Meeeeeeee
8-Meeeeeeeeeeeeeeeee (88, M8 = 8-Mee); Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.
Me 8-eeeeeee eeeeeee (88; 888.8 ee, 8 eeee) ee MMM (8 eM) eee eeeee e eeee ee 8.8 M 8-eeeeeeeeeeeeee eeeeeee (88, M8 = 8-Mee; 8 eeee) ee MMM (8 eM) ee 8°M eeeee M8. Meeee 88 eee, eee eeeeeee eee eeeeeeee eeee eee. ee MM8Me (88 eM) eee eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeee (MeMM8) eee eeeeeeeeee ee eeeeeee eeeee eeeeee. Mee eeeee eeeeeee eee eeeeeeee ee Meeeeeeee eeeeeeeeeeee (88–88°M/8 Meee) ee eeeeee eeee eeeeeee; eeeee: 888.8 ee (88%).
8,8-Meeeeeee-8,8-eeeee-8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-eeeeeeeeeeee (88); Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.
M 8.8 M eeee ee eMeMeMe (8.88 eeee) ee MMM (8.88 eM) eee eeeee eeeeeeee eeee 8 eee ee e eeeeeee eeee ee eee eeeeee 88 (888 ee, 8.88 eeee) ee MMM (88 eM) ee −88°M eeeee eeeee. Mee eeeeeeeee eeee eee eeee eeeeeee eee 88 eee, eee MeMM (8; 888 ee, 8.88 eeee) eee eeeee. Mee eeeeeeee eee eeeeeee ee eeee ee ee, eeeee (88 eM) eee eeeee, eee eee eeeeeee eee eeeeee ee ee eeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/Me8M 8:8) ee eeee 88 ee e eeeee eeeee; eeeee: 888 ee (88%); ee 888°M.
References
| [14] | Mee, M. M.; Mee, M. M., Meeee. Meeeee., (8888) 88, 8888. |
| [15] | Meeeeee, M.; Meeeeäeeee, M.; Meeeee, M.; Meeeeee, M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
| [16] | Méeeeeee, M.; Meeeêeee, M.; Meeee, M.; Meé, M.; Meéeeeeee, M.; Meeeee, M.; Meeeeee, M., Meeeeee, (8888), 8888. |
| [17] | Meeeeee, M.; Meeeeeeee, M.; Méeeeeee, M.; Meeeee, M.; Meeeeäeeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [18] | Meeeeee, M.; Meeeeee, M., Meeeeee, (8888), 8888. |
| [19] | Meee, M.; Meeeee, M.; Meeeee, M.; Meeeeee, M., Mee. Meee., (8888) 8, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) 88/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 8888.
Return to Top