Stereospecificity in the Gas Phase. Formation and Characterization of Configurationally Stable Cyclopropyl Anions

Michael C. Baschky, Kent C. Peterson, Steven R Kass

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

We report the gas-phase preparation of cis- and (raiu-β-formylcyclopropyl anion (4c and 4t) via the room temperature fluorodesilylation of their corresponding trimethylsilyl derivatives. These homoenolates do not interconvert or undergo ring-opening isomerization at 25 °C, and can readily be differentiated with several chemical probes. The proton affinities of both 4c and 4t have been measured, and the results are compared to ab initio computations. Cyclization to a 2-bicyclobutoxide ion (8) has been considered, and although the process is calculated to have a small activation barrier, it is found to be thermodynamically unfavorable.

Original languageEnglish (US)
Pages (from-to)7218-7224
Number of pages7
JournalJournal of the American Chemical Society
Volume116
Issue number16
DOIs
StatePublished - Aug 1 1994

Fingerprint Dive into the research topics of 'Stereospecificity in the Gas Phase. Formation and Characterization of Configurationally Stable Cyclopropyl Anions'. Together they form a unique fingerprint.

Cite this