Syntheses and regiochemistry of enol addition to 9-phenyl-9H-xanthen-9-ol

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
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ID Code:113943
Deposited On:30 Apr 2018 12:22
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