Abstract
trans-2-Benzal-4,4-dimethyl-1-tetralone (Ib) and its endocyclic unsaturated isomer IXb were synthesized in good yields and characterized by their chemical properties and absorption spectra. The structure of 2-benzal-4,4-dimethyl-1-tetralone oxide (VIIb) obtained by alkaline epoxidation of Ib was verified by synthesis through a Darzens condensation. The advantage of 80% sulfuric acid in the condensation of o-nitrobenzaldehyde with 1-tetralone and 1-indanone was demonstrated. Analogies between 2-benzal-1-tetralones, 2-benzal-1-indanone and chalcones are pointed out and a discussion is presented of the effect of conjugation, α-bromo substitution and 4-gem-dimethyl substitution in 1-tetralones in terms of conformational analysis, ultraviolet and infrared absorption characteristics.
| Original language | English |
|---|---|
| Pages (from-to) | 893-900 |
| Number of pages | 8 |
| Journal | Journal of the American Chemical Society |
| Volume | 80 |
| Issue number | 4 |
| DOIs | |
| State | Published - 1958 |
| Externally published | Yes |