An investigation of the interaction of 4-membered rings with adjacent carbanion centers

Date

2002-01-01

Author

Guven, OO
Peynircioğlu, Nihad Bekir

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A series of cyclobutylcarbinyl phenyl ketones was prepared and the rates of base catalyzed hydrogen-deuterium exchange of a-hydrogen atoms were compared with those of appropriate model compounds, to test the validity of an earlier finding, which suggested that a four-membered ring, like the three-membered ring, has the ability to stabilize an adjacent carbanion center. In this study, unlike the cyclopropyl group, no clearly defined stabilization of the adjacent, carbanion center was detected by the 1-phenyl- and 1-p-nitrophenyl- substituted cyclobutyl groups and only a very slight rate enhancement by the 3-phenylcyclobutyl group was detected. Attempts to detect a stabilization of the carbanion center by a cyclobutyl-substituted methyl group (homoconjugative interaction) also failed.

Subject Keywords

Carbanions, Cyclobutylcarbinyl, Strained molecules

URI

https://hdl.handle.net/11511/53462

Journal

TURKISH JOURNAL OF CHEMISTRY

Collections

Department of Chemistry, Article

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Citation Formats

O. Guven and N. B. Peynircioğlu, “An investigation of the interaction of 4-membered rings with adjacent carbanion centers,” TURKISH JOURNAL OF CHEMISTRY, pp. 153–158, 2002, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/53462.