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Structural effects on sigmatropic shifts in heteroaromatic allyl ethersElectron...
Araújo, Nuna C.; Barroca, Pedro M. M.; Bickley, Jamie F.; Brigas, Amadeu F.; Cristiano, Maria Lurdes Santos; Johnstone, Robert A. W.In contrast to the known thermal, exclusively [3,3], O- to N- rearrangement of allyl groups in phenyltetrazoles (1, Scheme 1), the comparable migration of the allyl group in pseudosaccharyl ethers (3; Scheme 2) has been shown to proceed through both [1,3]- and [3,3]-mechanisms, 4, 5; for the pseudosaccharyl derivative of the natural product myrtenol (6; Scheme 3) only the product 7 of a [1,3]-shift has been obs...
Diels–alder reactions of alkyl 2H-azirine-3-carboxylates with furans
Alves, M. José; Azoia, Nuno G.; Bickley, Jamie F.; Fortes, A. Gil; Gilchrist, Thomas L.; Mendonça, RicardoMethyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate 1 and furan give the aziridine 2 by a Diels–Alder cycloaddition reaction. The hydrolysis of compound 2 leads to a dihydrofuranol 11 by cleavage of a C–N bond. X-Ray crystal structures of compounds 2 and 11 have been determined. Compound 2 reacts with alcohols in a similar way to give 2-alkoxy-2,5-dihydrofurans as mixtures of cis and trans isomers. The struc...
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