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Synthesis 2012; 44(23): 3671-3677
DOI: 10.1055/s-0032-1317497
DOI: 10.1055/s-0032-1317497
paper
Synthesis of Chromanes and 4H-Chromenes: Exploring the Oxidation of 2H-Chromenes and Dihydro-1-benzoxepines by Hypervalent Iodine(III)
Weitere Informationen
Publikationsverlauf
Received: 09. August 2012
Accepted: 02. Oktober 2012
Publikationsdatum:
17. Oktober 2012 (online)
![](https://www.thieme-connect.de/media/synthesis/201223/lookinside/thumbnails/10.1055-s-0032-1317497-1.jpg)
Abstract
The reaction of various oxygen-containing benzo-fused cycloalkenes were studied with the hypervalent iodine reagent hydroxy(tosyloxy)iodo]benzene [PhI(OH)OTs, HTIB]. 2H-Chromene and 4-methyl-2H-chromene resulted in substituted 4H-chromene and cis-3,4-dialkoxy-4-methyl-3,4-dihydro-2H-chromenes, respectively. Ring contraction to chromanes and benzofurans was observed for dihydrobenzoxepines and 2,2-dimethyl-2H-chromenes, respectively.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
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For books, see:
For reviews see refs 4c–e:
For recent examples see refs 4f–j:
Some additional tests for 5a:
Some additional tests for 5b:
Some additional tests for 5f:
Some additional tests for 5g: