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Small-Ring Compounds. XVII. 2-Hydroxy-3-phenyl-2-cyclobutenone and Related Substances

Silversmith, Ernest F. and Roberts, John D. (1958) Small-Ring Compounds. XVII. 2-Hydroxy-3-phenyl-2-cyclobutenone and Related Substances. Journal of the American Chemical Society, 80 (15). pp. 4083-4085. ISSN 0002-7863. doi:10.1021/ja01548a064.

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1,1,2-Trifluoro-2-chloro-3-phenylcyclobutane (I ) undergoes dehydrohalogenation with one mole of ethanolic potassium hydroxide and is converted to 1,1,2-trifluoro-3-phenyl-2-cyclobutene (II). With excess ethanolic potassium hydroxide, I, II or 1,1,2,2-tetrafluoro-3-phenylcyclobutane (IV) yield 1,1-difluoro-2-ethoxy-3-phenyl-2-cyclobutene (III). Hydrolysis of III in 92% sulfuric acid affords 2-ethoxy-3-phenyl-2-cyclobutenone (V) which is rather more stable toward acid hydrolysis than ordinary vinyl ethers. Treatment of I with excess potassium-butoxide in t-butyl alcohol yields 1.1-difluoro-2-t-butoxy-3-phenyl-2-cyclobutene (VI) which, on acid hydrolysis, gives 2-hydroxy-3-phenyl-2-cyclobutenone (VII). The pK_A of VII was found to be 3-4 units lower than the pK_A's of 2-hydroxy-2-cyclopentenone and 2-hydroxy-2-cyclohexenone.

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Additional Information:© 1958 American Chemical Society. Received January 9, 1958. Supported in part by a grant from the National Science Foundation. National Science Foundation Postdoctoral Fellow, 1955-1956.
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NSF Postdoctoral FellowshipUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry2258
Issue or Number:15
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Official Citation:Small-Ring Compounds. XVII. 2-Hydroxy-3-phenyl-2-cyclobutenone and Related Substances Ernest F. Silversmith and John D. Roberts Journal of the American Chemical Society 1958 80 (15), 4083-4085 DOI: 10.1021/ja01548a064
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61345
Deposited By: Ruth Sustaita
Deposited On:20 Oct 2015 22:56
Last Modified:10 Nov 2021 22:47

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