Novel oxa-di-pi-methane and Norrish type I reactions in the S2 (pi,pi*) excited state of a series of beta,gamma-unsaturated ketones

Diego Armesto; Maria J Ortiz; Antonia R Agarrabeitia; Mar Martín-Fontecha

doi:10.1021/ol050846d

Novel oxa-di-pi-methane and Norrish type I reactions in the S2 (pi,pi*) excited state of a series of beta,gamma-unsaturated ketones

Org Lett. 2005 Jun 23;7(13):2687-90. doi: 10.1021/ol050846d.

Authors

Diego Armesto¹, Maria J Ortiz, Antonia R Agarrabeitia, Mar Martín-Fontecha

Affiliation

¹ Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense, 28040 Madrid, Spain. [email protected]

PMID: 15957922
DOI: 10.1021/ol050846d

Abstract

[reaction: see text] Beta,gamma-unsaturated methyl ketones with electron-withdrawing groups at the gamma-position of the ene moiety undergo ODPM rearrangements and Norrish type I reactions on direct irradiation at 254 nm. The results are consistent with the involvement of alkene S(2) (pi,pi*) as reactive excited states in these processes.