Synthesis of thiiranes by rhodium-catalyzed sulfur addition reaction to reactive alkenes

Mieko Arisawa; Takuya Ichikawa; Masahiko Yamaguchi

doi:10.1039/c5cc01570g

Synthesis of thiiranes by rhodium-catalyzed sulfur addition reaction to reactive alkenes

Mieko Arisawa, Takuya Ichikawa, Masahiko Yamaguchi

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

A rhodium complex derived from RhH(PPh₃)₄, dppe, and 4-ethynyltoluene catalyzes the addition reaction of sulfur to norbornenes giving the corresponding thiiranes under acetone reflux conditions. The rhodium complex effectively transfers a sulfur atom to the double bond from sulfur, and exo-adducts are obtained. The reaction is also applicable to (E)-cyclooctene and cyclic allenes. The ring-opening reaction of the thiiranes with lithium aluminium hydride gives the corresponding thiols. This journal is

Original language	English
Pages (from-to)	8821-8824
Number of pages	4
Journal	Chemical Communications
Volume	51
Issue number	42
DOIs	https://doi.org/10.1039/c5cc01570g
Publication status	Published - May 25 2015
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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T1 - Synthesis of thiiranes by rhodium-catalyzed sulfur addition reaction to reactive alkenes

AU - Arisawa, Mieko

AU - Ichikawa, Takuya

AU - Yamaguchi, Masahiko

N1 - Publisher Copyright: © The Royal Society of Chemistry.

PY - 2015/5/25

Y1 - 2015/5/25

N2 - A rhodium complex derived from RhH(PPh3)4, dppe, and 4-ethynyltoluene catalyzes the addition reaction of sulfur to norbornenes giving the corresponding thiiranes under acetone reflux conditions. The rhodium complex effectively transfers a sulfur atom to the double bond from sulfur, and exo-adducts are obtained. The reaction is also applicable to (E)-cyclooctene and cyclic allenes. The ring-opening reaction of the thiiranes with lithium aluminium hydride gives the corresponding thiols. This journal is

AB - A rhodium complex derived from RhH(PPh3)4, dppe, and 4-ethynyltoluene catalyzes the addition reaction of sulfur to norbornenes giving the corresponding thiiranes under acetone reflux conditions. The rhodium complex effectively transfers a sulfur atom to the double bond from sulfur, and exo-adducts are obtained. The reaction is also applicable to (E)-cyclooctene and cyclic allenes. The ring-opening reaction of the thiiranes with lithium aluminium hydride gives the corresponding thiols. This journal is

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Synthesis of thiiranes by rhodium-catalyzed sulfur addition reaction to reactive alkenes

Abstract

All Science Journal Classification (ASJC) codes

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