The chemistry of derivatives of 2-benzaltetralone. H. Absorption spectra and stereostructure

Alfred Hassner, Norman H. Cromwell

Research output: Contribution to journalArticlepeer-review


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 languageEnglish
Pages (from-to)893-900
Number of pages8
JournalJournal of the American Chemical Society
Issue number4
StatePublished - 1958
Externally publishedYes


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