Computational discovery of a novel automerization process for 1-fluorocyclopropene

William R Dolbier Jr; G Robert Shelton; Merle A Battiste; John F Stanton; David R Price

doi:10.1021/ol0169574

Computational discovery of a novel automerization process for 1-fluorocyclopropene

Org Lett. 2002 Jan 24;4(2):233-5. doi: 10.1021/ol0169574.

Authors

William R Dolbier Jr¹, G Robert Shelton, Merle A Battiste, John F Stanton, David R Price

Affiliation

¹ Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. [email protected]

PMID: 11796058
DOI: 10.1021/ol0169574

Abstract

[reaction: see text] Both DFT and CCSD and CCSD(T) computational methods indicate that 1-fluorocyclopropene can undergo an unprecedented "electrocyclic" automerization process involving a full 180 degrees rotation of its methylene group, without the formation of an intermediate carbene or diradical.