Heterocyclic rearrangements in constrained media. A zeolite-directed photorearrangement of 1,2,4-oxadiazoles.

J Org Chem

Dipartimento di Chimica Organica "E. Paterno", Università degli Studi di Palermo, Viale delle Scienze-Parco d'Orleans II, I-90128 Palermo, Italy.

Published: March 2005

[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.

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Source
http://dx.doi.org/10.1021/jo047910+DOI Listing

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