Abstract
The preparation of the relatively unknown 7-cis isomers of β-ionyl and β-ionylidene derivatives via one way sensitized geometric isomerization is described. These highly sterically crowded isomers, once prepared do not readily thermally revert back to the trans. But the trienes, at temperatures ≥ 100° undergo irreversible cyclization to cyclohexadienes. 7-cis Isomers of β-ionylideneacetone and acetaldehyde as well as higher tetraenes and pentaenes in this series could not be prepared by sensitized isomerization. Partial reduction of 7-cis-β-ionylideneacetonitrile isomers led to the preparation of 7-cis- and 7,9-dicis-β-ionylideneacetaldehyde; and methyl Grignard reaction with the same nitrile gave the triene-methyl ketones.
Original language | English (US) |
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Pages (from-to) | 193-199 |
Number of pages | 7 |
Journal | Tetrahedron |
Volume | 31 |
Issue number | 3 |
DOIs | |
State | Published - 1975 |
Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry