Formation of macrocyclic lactones in the Paternò-Büchi dimerization reaction.
Beilstein J Org Chem
; 7: 265-9, 2011 Feb 28.
Article
em En
| MEDLINE
| ID: mdl-21448243
ABSTRACT
Furan-2-ylmethyl 2-oxoacetates 1a,b, in which the furan ring and the carbonyl moiety were embedded intramolecularly, were synthesized from commercially available furan-2-ylmethanol and their photochemical reaction (hν > 290 nm) was investigated. Twelve-membered macrocyclic lactones 2a,b with C(i) symmetry including two oxetane-rings, which are the Paternò-Büchi dimerization products, were isolated in ca. 20% yield. The intramolecular cyclization products, such as 3-alkoxyoxetane and 2,7-dioxabicyclo[2.2.1]hept-5-ene derivatives, were not detected in the photolysate.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2011
Tipo de documento:
Article