Heterocyclic rearrangements in constrained media. A zeolite-directed photorearrangement of 1,2,4-oxadiazoles.
[reaction: see text] The first intrazeolite-photoinduced rearrangement of a five-membered heterocycle is reported. A completely different behavior compared to solution irradiations has been observed. The zeolite's role in directing the photoreaction of 3-phenyl-1,2,4-oxadiazoles toward the formation of the corresponding 1,3,4-oxadiazoles in a ring contraction-ringexpansion route is discussed.
Pace
Andrea
A
Dipartimento di Chimica Organica "E. Paterno", Università degli Studi di Palermo, Viale delle Scienze-Parco d'Orleans II, I-90128 Palermo, Italy. pace@unipa.it
Buscemi
Silvestre
S
Vivona
Nicolo
N
D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000528:radiation effects; D010777:Photochemistry; D014466:Ultraviolet Rays; D017641:Zeolites / Q000737:chemistry*
D010069:Oxadiazoles; D017641:Zeolites