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Synthesis 2009(22): 3848-3852
DOI: 10.1055/s-0029-1217016
DOI: 10.1055/s-0029-1217016
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Concise, Novel Route to 1,3-Benzoxathian Derivatives
Weitere Informationen
Received
7 April 2009
Publikationsdatum:
23. September 2009 (online)
Publikationsverlauf
Publikationsdatum:
23. September 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200922/lookinside/thumbnails/10.1055-s-0029-1217016-1.jpg)
Abstract
Novel 1,3-benzoxathian derivatives were successfully prepared in a one-pot process via a tandem ring-closure/β-elimination pathway from easily accessible o-thio-substituted phenols.
Key words
1,3-Benzoxathian - annulation - phenols - ring-closure - elimination
- 1
Katada T.Eguchi S.Esaki T.Sasaki T. J. Chem. Soc., Perkin Trans. 1 1984, 2649 - 2
Page PCB.Lund A. Comprehensive Heterocyclic Chemistry II Vol. 6:Katrizky AR.Rees CW.Scriven EFV. Pergamon; Oxford: 1996. p.415-445 - 3
Arnoldi A.Bassoli A.Merlini L.Ragg E. J. Chem. Soc., Perkin Trans. 1 1993, 1359 - 4
Magnus P.Mitchell IS. Tetrahedron Lett. 1998, 39: 9131 -
5a
Burdon MG.Moffatt JG. J. Am. Chem. Soc. 1965, 87: 4656 -
5b
Burdon MG.Moffatt JG. J. Am. Chem. Soc. 1965, 87: 4658 -
5c
Burdon MG.Moffatt JG. J. Am. Chem. Soc. 1966, 88: 5855 -
5d
Hayashi Y.Oda R. J. Org. Chem. 1967, 32: 457 -
5e
Burdon MG.Moffatt JG. J. Am. Chem. Soc. 1967, 89: 4725 - For discussions on the mechanism, see:
-
6a
Olofson RA.Marino JP. Tetrahedron 1971, 27: 4195 -
6b
Marino JP.Pfitzner KE.Olofson RA. Tetrahedron 1971, 27: 4181 - 7
Pizzoli F,Luisoli R,Knobloch G, andMeier H.-R. inventors; EP Patent 1116714A1. ; Chem. Abstr. 2001, 135, 95009 - 8
Heuer H.-W,Wehrmann R, andBruder F.-K. inventors; US Patent 0090593. ; Chem. Abstr. 2005, 142, 280926 - 9
Moffat JG. inventors; US Patent 3457315. ; Chem. Abstr. 1970, 72, 90051
References
PP powder (1.3 kg) was blended with Irganox 1010 (0.05%), calcium stearate (0.05%), Irgafos 168 (0.02%) and the 1,3-benzoxathian derivative (0.02%). The blend was extruded in an extruder having a cylinder diameter of 20 mm and a length of 400 mm at 100 rpm. The three heating zones being adjusted to the following temperatures: 260, 270 and 280 ˚C. The extrudate was cooled down, granulated and extruded again. After three extrusions, the MFI was measured at 230 ˚C/2.16 kg.