Open AccessStructural 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/
Author(s) -
Nuna Araújo,
Pedro M. M. Barroca,
J.F. Bickley,
A. F. Brigas,
Maria L. S. Cristiano,
R. A. W. Johnstone,
Rui M. S. Loureiro,
Paula C. A. Pena
Publication year - 2002
Publication title -
journal of the chemical society perkin transactions 1
Language(s) - English
Resource type - Journals
eISSN - 1472-7781
pISSN - 1364-5463
DOI - 10.1039/b102674g
Subject(s) - sigmatropic reaction , chemistry , isomerization , derivative (finance) , selectivity , product (mathematics) , stereochemistry , computational chemistry , organic chemistry , mathematics , catalysis , geometry , financial economics , economics
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
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom