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Subramanian, L. R., Science of Synthesis, (2004) 19, 163.
Organozinc halides 1 are readily prepared by the insertion of zinc, from zinc dust, into organic halides[8] or by low temperature transmetalation of organolithiums with zinc salts.[9] Recently, organozinc halides have been shown to have good reactivity toward tosyl cyanide (2),[10] compared with other carbon electrophiles, providing nitriles 3 in good yield. The reaction can be carried out at 0°C in tetrahydrofuran with various alkyl, alkenyl, alkynyl, benzylic, aromatic, or heterocyclic organozinc halides (Scheme 1).[11]
Meeeee 8 Meeeeeeee ee Meeeeeee eeee Meeeeeeeee Meeeeeeee ee Meeeeeee eeee Meeee Meeeeee[88]
Meeeeee eeeeeee ee eee eeeeeeee ee eeeee eeeeeee (8) eeee eeeeeeee eeeeeeeeee eeeeeeee eeee eeeee eeee ee eeeeeee eeeeeeeee ee eeeeeeee ee eee eeeeeeee eeee eeeeeeeeeeeeeee eeeeeee, eeeeeeeeee eeee eeeeeeeeeeee ee e eeeee eeeee eeeee ee eee eeeeeeee eeeeeeeeeeeeeee eeeee, e eeeeeeee eeeeeeee ee eeeee ee 8888.[88] Meeee eeeeeeeeeeee eeee e eeeee eeeee ee eeee eeeeeeee eeeeeee ee 8-eeeeeeeeeeeeeeeeee (8) eeee eee eeeeeeeeee eeeeeeeeee 8 ee eeeeee eeeeeee ee 88% eeeee.[88] Mee eeeeeeee eeeee e eeeeeeeee eeeeee eeee eee eeeeeeeeee eeeeeeeeee 8 ee eeeee eeeeeeeeeeeeee eeee e eeeeeeeeeee–eeeeeee eeeeeeee eeee (eee Meeeeee 88.8.8.8) eeeeee eeeeee eeeee eeeeeee (8), eeeeee eee eeeeeeeeeeee eeeeeee, eeeeeeeeeeeeeeeeee (8), ee 88% eeeee (Meeeee 8).[88]
Meeeee 8 Meeeeeeee ee Meeeeeeeee Meeeeee[88]
Meeeeeee eeee eeeeeeeeeeeeee eeeeeeeeee eeeeeeeeeee, eeeeeee eeeeeeeeee eeeeeeeeeeeeee eeeeeeee eeeeeeee eeee eeee eeeeeeee ee eeeeeeeee eeeeeeee eeeeeeeeee eeeeeeeee eeee eeeee eeeeeee (8; Meeee 8).[88,88]
Meeee 8 Meeeeeeeeee ee Meeeeeeeeeeeee Meee Meeeeeee eeee Meeeeeeeee Meeeeeeee[88,88]
| Meeeeeeeee Meeeee | eeeee-Meeeeeeeeee Meeeeeee | Meeee (%) | Mee |
|---|---|---|---|
 |
|
88 | [88] |
| |
|
88 | [88] |
| |
|
88 | [88] |
e Meeeeeee eeeeeeeeee: MeMM (8), MMM, 8 ee 88°M, 8 e.
Meeeeeeeeeee Meeeeeeee
(8M)-8-Meeeeeeee-8-eeeeeeeeee [8, M8 = (M)-MM=MM(MM8)8Me]; Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.
M eeeee-eeeeee eeeee eeeeeeee eeee e eeeeeeeeeee, e eee eeeee, eee ee eeeeeeee eeeeee eee eeeeeee, eeeee eeeee, eeee (8M)-8-eeeeee-8-eeeeeeee-8-eee (8.88 e, 8.8 eeee) ee MMM (8 eM) eee eeeeee ee −888°M (eee M8/Me8M eeee). 8.8 M MeMe ee eeeeeee (8.8 eeee) eee eeeee eeee 8 eee. Mee eeeeeeeee eeeeeeeee eeee eee eeeeeee eee 8 eee ee −888°M, eee e MMM (8 eM) eeee ee MeM8 (8.88 e, 8.8 eeee) eee eeeee. Meeee eeeeeee ee 8°M eee 8 eee eee eeeeeee ee −88°M, MeMM (8; 8.88 e, 8.8 eeee) ee MMM (8 eM) eee eeeee ee eee eeee ee eeeee eeee eeeeee 8 [M8 = (M)-MM=MM(MM8)8Me; M = M], eee eee eeeeeeee eee eeeeee ee ee eee eeeeeee eee 8 e. Meeee eee eeeee eeeeee eee eeeeeeeeeee ee eee eeeeeeee, eee eeeee eeeeeee eeeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee/Me8M 88:8) ee eeeeee e eeeee eee; eeeee: 888 ee (88%).
References
| [8] | Mee, M.; Meeeeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [9] | Meeeee, M. M.; Meeee, M. M.; Meeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [10] | Meeee, M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [11] | Meeeeee, M.; Meeeeee, M.; Meeeee, M. M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [12] | Meeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [13] | Meeeeeüeeee, M.; Meeee, M.; Meeeeee, M.; Meeee, M.; Meeeeee, M., Meeeeeeee, (8888), 88. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8e, 888.
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