A NEW AND EFFECTIVE METHOD FOR THE LOW-TEMPERATURE GENERATION OF SULFONIUM YLIDES FROM ALLYL SULFIDES

Authors
HARTLEY RC WARREN S RICHARDS IC
Citation
Rc. Hartley et al., A NEW AND EFFECTIVE METHOD FOR THE LOW-TEMPERATURE GENERATION OF SULFONIUM YLIDES FROM ALLYL SULFIDES, Journal of the Chemical Society. Perkin transactions. I, (5), 1994, pp. 507-513
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
5
Year of publication
1994
Pages
507 - 513
Database
ISI
SICI code
0300-922X(1994):5<507:ANAEMF>2.0.ZU;2-K
Abstract
Allyl 4-methoxyphenyl sulfides can be converted into sulphonium ylides which undergo [2,3] sigmatropic rearrangement in high yield and with excellent stereoselectivity by repeated alternate additions of a diazo nium salt and tetrafluoroboric acid at low temperature. Under these co nditions, side reactions are suppressed and both cyclic and open-chain compounds, including one containing a tertiary amine, give homoallyli c sulfides in good yield. Epoxides may be made from the products.