Reaction of a Highly Spiro-activated Electrophilic Cyclopropane with Pyridines; an Unusual Solvent Effect on Reaction Rate

DOI: 10.1039/P29860000043

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Journal of the Chemical Society. Perkin transactions II p. 43 - 48 (1986)

Update date:2022-08-05

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Authors:

Ohkata, Katsuo

Nagai, Takashi

Tamaru, Akira

Hanafusa, Terukiyo

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Article abstract of DOI:10.1039/P29860000043

The kinetics of the reaction of 3,3,10,10-tetramethyldispiro<5.0.5.1>tridecane-1,5,8,12-tetraone (1) with pyridine was studied in various pure solvents (protic and aprotic).Although this reaction afforded a polar zwitterion , the solvent effect on the reaction rate was not as remarkable as that in the Menschutkin reaction; it was related to Gutmann's DN parameters rather than to the Dimroth-Reichardt E_T values.The multiparameter analysis approach according to the Krygowski-Fawcett model in aprotic solvents and the Taft-Kamlet model in protic solvents was successful, giving log k₂ = -8.82 X E-3E_T - 17.4 X E-3DN - 3.36 (r = 0.927; n = 8) and log k₂ = -0.734α + 0.162β - 3.15 (r = 0.941; n = 6), respectively.Mechanisms are discussed.

Full text of DOI:10.1039/P29860000043

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