Abstract
Reaction of aliphatic aldehyde phenylhydrazones with methyl acrylate or acrylonitrile gives phenylazoalkanes (1) by an ene reaction. With more electron-deficient alkenes such as methyl vinyl ketone or β-nitrostyrene, Michael reaction at nitrogen occurs followed by cyclization to give pyrazolidines. The reactions of phenylhydrazone monoanions with acrylonitrile take a variety of pathways depending on the counterion. The cuprous salt reacts from carbon to give 1, the lithium salt initiates polymerization, and the diethylaluminum salt alkylates on nitrogen.
| Original language | English |
|---|---|
| Pages (from-to) | 218-221 |
| Number of pages | 4 |
| Journal | Journal of Organic Chemistry |
| Volume | 44 |
| Issue number | 2 |
| DOIs | |
| State | Published - 1979 |
| Externally published | Yes |