Kavala, Veerababurao ; Murru, Siva ; Das, Gopal ; Patel, Bhisma K. (2008) Syntheses and regiochemistry of enol addition to 9-phenyl-9H-xanthen-9-ol Tetrahedron, 64 (18). pp. 3960-3965. ISSN 0040-4020
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Official URL: https://www.sciencedirect.com/science/article/pii/...
Related URL: http://dx.doi.org/10.1016/j.tet.2008.02.053
Abstract
Regioselective C–C bond formation of 9-phenyl-9H-xanthen-9-ol 1 with various enolizable ketones I–X in an acidic (HBr) medium, obtained by the reaction of 1,1′-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) with ketone is observed. Except for ketone, 4-methyl-pentan-2-one VII in all other cases examined the attack to xanthenyl carbocation is from the thermodynamically stable enolizable side of the unsymmetrical ketones. In the case of 3-methyl-butan-2-one VIII the equilibrium is in favor of the more stable enolizable ketone, which has large steric factor, hence no reaction was observed during its addition to alcohol 1.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 113943 |
| Deposited On: | 30 Apr 2018 12:22 |
| Last Modified: | 30 Apr 2018 12:22 |
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