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Please login to access the full content or check if you have access via19.5.2.1.1 Variation 1: By Alkylation Followed by Basic Cleavage
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Subramanian, L. R., Science of Synthesis, (2004) 19, 109.
Replacing strongly alkaline conditions[1] with the mild base, 1,5-diazabicyclo[5.4.0]undec-5-ene, in the reaction of iodomethane with the dimethylhydrazones of aldehydes produces nitriles in fairly good yields.[2] Thus, reaction of excess iodomethane with dimethylhydrazones 1 followed by reaction with neat 1,5-diazabicyclo[5.4.0]undec-5-ene at room temperature affords nitriles 2 (Scheme 1). The chiral nitrile 4 has been prepared by this method from the (S)-1-amino-2-(methoxymethyl)pyrrolidine (SAMP) hydrazone 3 (Scheme 2).
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References
| [1] | Meeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [2] | Meeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
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