Uses
Tropone has been used in synthesis of:
- bicyclic δ-lactones via heterocyclic carbine-catalyzed [8+3] annulation pathway
- 6,7-benzobicyclo [3.2.2] nona-3,6,8-trien-2-one via thermal addition to bezyne
Application
Tropone can be used to prepare the synthon of cycloheptadiene-1-one; it is used as the basis for the synthesis of cycloheptadiene compounds, fluorene compounds, polycyclic compounds, and natural products.
Preparation
2,4,6-cycloheptatrien-1-one (1) is a functionalized conjugated carbocyclic compound with diversified reactivity. The most popular and simple method of preparation involves oxidation of 1,3,5- Cycloheptatriene with Selenium(IV) Oxide-KH2PO4. Several other procedures have also been developed, among which electrooxidation of cycloheptatrienes and α-pyrone ring expansion via high-pressure cycloaddition of cyclopropenone acetals can be considered general methods of synthesis of tropones.
Synthesis Reference(s)
Journal of the American Chemical Society, 78, p. 5442, 1956
DOI: 10.1021/ja01601a077The Journal of Organic Chemistry, 29, p. 960, 1964
Organic Syntheses, Coll. Vol. 9, p. 396, 1998
General Description
Metal-catalyzed [6+3] cycloaddition of tropone with azomethine ylides has been reported.
