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Stereochemistry of cyclopropane ring opening in the acid-catalyzed fragmentation of endo-8-tricyclo[3.2.1.02,4]octanone

✍ Scribed by Merle A. Battiste; Judith Mackiernan

Publisher: Elsevier Science
Year: 1972
Tongue: French
Weight: 145 KB
Volume: 13
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)94246-7

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✦ Synopsis

The reported instances of inversion of configuration in the acid-catalyzed opening of cyclopropane rings are rare.2 The recent report' of exclusive inversion in the hydrogen chloride promoted opening of a fused cyclopropane ring prompts us to amplify our previous observations4 of a similarly striking stereochemical result in the acid-catalyzed fragmentation of endo-8-tricyclo[3.2.1.

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