1,3-oxathiane ring formation through intramolecular Pummerer reaction of alkyl ortho-hydroxymethylphenyl sulfoxides

Authors
Abe, H Shibaike, K Fujii, H Tsuchida, D Akiyama, T Harayama, T
Citation
H. Abe et al., 1,3-oxathiane ring formation through intramolecular Pummerer reaction of alkyl ortho-hydroxymethylphenyl sulfoxides, HETEROCYCLE, 50(1), 1999, pp. 291-298
Citations number
30
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
50
Issue
1
Year of publication
1999
Pages
291 - 298
Database
ISI
SICI code
0385-5414(19990101)50:1<291:1RFTIP>2.0.ZU;2-L
Abstract
The intramolecular Pummerer rearrangement of 2-(2-alkylsulfinylphenyl)-2-pr opanols (1a, 1c-1g) yielded 1,3-oxathianes (2a, 2c-2g) in the presence of p -toluenesulfonic acid and molecular sieves 3A. Alkyl halides were converted into 1,3-oxathiane derivatives in three steps via this rearrangement.