Abstract
1,3-Dienic δ-sultones 4,6-diaryl-[1,2]oxathiine 2,2-dioxides were synthesized via a one-step reaction of arylalkynes with dioxane sulfotrioxide. The reactivity of various alkynes in this reaction was investigated. The resulting sultones were brominated with Br2 or N-bromosuccinimide regioselectively to sulfur and subsequently coupled with phenylacetylene using Sonogashira conditions.
| Original language | English |
|---|---|
| Pages (from-to) | 3-16 |
| Number of pages | 14 |
| Journal | Journal of Sulfur Chemistry |
| Volume | 32 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - Feb 2011 |
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Keywords
- δ-sultones
- alkynes
- bromination
- dioxane sulfotrioxide
- Sonogashira coupling
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Simple and practical one-step synthesis of new 1,3-dienic δ-sultones from terminal alkynes and some synthetic applications of these compounds. / Gaitzsch, Jens; Rogachev, Victor; Metz, Peter; Filimonov, Victor D.; Zahel, Martin; Kataeva, Olga.
In: Journal of Sulfur Chemistry, Vol. 32, No. 1, 02.2011, p. 3-16.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Simple and practical one-step synthesis of new 1,3-dienic δ-sultones from terminal alkynes and some synthetic applications of these compounds
AU - Gaitzsch, Jens
AU - Rogachev, Victor
AU - Metz, Peter
AU - Filimonov, Victor D.
AU - Zahel, Martin
AU - Kataeva, Olga
PY - 2011/2
Y1 - 2011/2
N2 - 1,3-Dienic δ-sultones 4,6-diaryl-[1,2]oxathiine 2,2-dioxides were synthesized via a one-step reaction of arylalkynes with dioxane sulfotrioxide. The reactivity of various alkynes in this reaction was investigated. The resulting sultones were brominated with Br2 or N-bromosuccinimide regioselectively to sulfur and subsequently coupled with phenylacetylene using Sonogashira conditions.
AB - 1,3-Dienic δ-sultones 4,6-diaryl-[1,2]oxathiine 2,2-dioxides were synthesized via a one-step reaction of arylalkynes with dioxane sulfotrioxide. The reactivity of various alkynes in this reaction was investigated. The resulting sultones were brominated with Br2 or N-bromosuccinimide regioselectively to sulfur and subsequently coupled with phenylacetylene using Sonogashira conditions.
KW - δ-sultones
KW - alkynes
KW - bromination
KW - dioxane sulfotrioxide
KW - Sonogashira coupling
UR - http://www.scopus.com/inward/record.url?scp=79551583278&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=79551583278&partnerID=8YFLogxK
U2 - 10.1080/17415993.2010.537339
DO - 10.1080/17415993.2010.537339
M3 - Article
AN - SCOPUS:79551583278
VL - 32
SP - 3
EP - 16
JO - Journal of Sulfur Chemistry
JF - Journal of Sulfur Chemistry
SN - 1741-5993
IS - 1
ER -