Evidence of hydrogen migration in an alkylphenyldiazirine excited state

Yunlong Zhang; Jacek Kubicki; Matthew S Platz

doi:10.1021/ol101127c

Evidence of hydrogen migration in an alkylphenyldiazirine excited state

Org Lett. 2010 Jul 16;12(14):3182-4. doi: 10.1021/ol101127c.

Authors

Yunlong Zhang¹, Jacek Kubicki, Matthew S Platz

Affiliation

¹ Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, USA.

PMID: 20572673
DOI: 10.1021/ol101127c

Abstract

Ultrafast photolysis (350 nm) of alkylphenyldiazirines promotes the diazirine to the S(1) excited state. Solvent and substituent effects on the excited state lifetimes indicate that the S(1) state is highly polarized and undergoes a [1,2]-H shift in concert with nitrogen extrusion in cyclohexane.