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Nucleophilic cleavage of spiroactivated cyclopropanes.1. Kinetic and thermodynamic parameters for reaction of 6,6-dimethyl-2-phenyl-5,7-dioxaspiro[2,5]octane-4,8-dione (2) with pyridine.

✍ Scribed by Michael A. McKinney; Kathleen G. Kremer; Thomas Aicher

Publisher: Elsevier Science
Year: 1984
Tongue: French
Weight: 204 KB
Volume: 25
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)81603-8

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✦ Synopsis

Reaction of the title spiroactivated cyclopropane(2) with pyridine in acetonitrite yields a zwitterionic addition product.

The reaction is reversible which provides conditions under which rates and equilibria constants can be obtained along with the derived activation and thermodynamic parameters of reaction.

An extended Bronsted treatment affords a 8,,, value for the reaction of 2 with substituted pyridines.

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