Simple and practical one-step synthesis of new 1,3-dienic δ-sultones from terminal alkynes and some synthetic applications of these compounds

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	https://doi.org/10.1080/17415993.2010.537339 https://doi.org/10.1080/17415993.2010.537339
Publication status	Published - Feb 2011

Keywords

δ-sultones
alkynes
bromination
dioxane sulfotrioxide
Sonogashira coupling

ASJC Scopus subject areas

Chemistry(all)

Access to Document

Fingerprint Dive into the research topics of 'Simple and practical one-step synthesis of new 1,3-dienic δ-sultones from terminal alkynes and some synthetic applications of these compounds'. Together they form a unique fingerprint.

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 › peer-review

@article{e5f4ac79bbab45f2a580ccd184a1be31,

title = "Simple and practical one-step synthesis of new 1,3-dienic δ-sultones from terminal alkynes and some synthetic applications of these compounds",

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.",

keywords = "δ-sultones, alkynes, bromination, dioxane sulfotrioxide, Sonogashira coupling",

author = "Jens Gaitzsch and Victor Rogachev and Peter Metz and Filimonov, {Victor D.} and Martin Zahel and Olga Kataeva",

year = "2011",

month = feb,

doi = "10.1080/17415993.2010.537339",

language = "English",

volume = "32",

pages = "3--16",

journal = "Journal of Sulfur Chemistry",

issn = "1741-5993",

publisher = "Taylor and Francis Ltd.",

number = "1",

}

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 -