Structural effects on sigmatropic shifts in heteroaromatic allyl ethersElectronic supplementary information (ESI) available: selected crystal data for compound 7. See http://www.rsc.org/suppdata/p1/b1/b102674g/

Araujo, Nuna C. P.; Barroca, Pedro M. M.; Bickley, Jamie F.; Brigas, Amadeu; Cristiano, Maria Lurdes Santos; Johnstone, Robert A. W.; Loureiro, Rui M. S.; Pena, Paula C. A.

http://hdl.handle.net/10400.1/4250

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Authors

Cristiano, Maria Lurdes Santos

Johnstone, Robert A. W.

Loureiro, Rui M. S.

Pena, Paula C. A.

Abstract(s)

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 observed; crystallographic data and theoretical calculations provide an explanation of this ease of [1,3]-isomerization and the observed selectivity as being due to conformational constraints and electronic factors.

URI

http://hdl.handle.net/10400.1/4250

Citation

Araújo, Nuna C. P.; Barroca, Pedro M. M.; Bickley, Jamie F.; Brigas, Amadeu F.; Cristiano, M. Lurdes S.; Johnstone, Robert A. W.; Loureiro, Rui M. S.; Pena, Paula C. A. Structural effects on sigmatropic shifts in heteroaromatic allyl ethersElectronic supplementary information (ESI) available: selected crystal data for compound 7. See http://www.rsc.org/suppdata/p1/b1/b102674g/, Journal of the Chemical Society, Perkin Transactions 1, 9, 1213-1219, 2002.