The Thiylation of Olefins

Prilezhaeva, E. N.; Shostakovskii, M. F.

doi:10.1070/rc1963v032n08abeh001351

Cited by 38 publications

(10 citation statements)

References 2 publications

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“…11 Sulfoxides are also important intermediates of many natural products. 12 Their synthesis has been achieved by means of a wide range of oxidising systems, starting from the corresponding sulfides.…”

Section: Introductionmentioning

confidence: 99%

Rare-earths as catalytic centres in organo-inorganic polymeric frameworksElectronic supplementary information (ESI) available: selected bond angles and hydrogen interactions in 1, 2, 3; coordination environment of the two scandium atoms in 1; coordination modes of the three crystallographically independent carboxylate groups for 2 and 3. See http://www.rsc.org/suppdata/jm/b3/b314220e/

et al. 2004

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New 3D polymeric succinates of rare-earths have been synthesised: [Sc 2 (C 4 and their structures solved by single crystal XRD. They were obtained as single phases, characterised and tested as heterogeneous catalysts as Lewis acids in the acetalization of aldehydes and as redox agents in the oxidation of sulfides showing them to be effective and selective catalysts, easy to recover and reusable. The scandium, yttrium and lanthanum oxides were also tested in the same catalytic reactions to prove the effect of the porous organo-inorganic framework.{ Electronic supplementary information (ESI) available: selected bond angles and hydrogen interactions in 1, 2, 3; coordination environment of the two scandium atoms in 1; coordination modes of the three crystallographically independent carboxylate groups for 2 and 3. See

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Section: Introductionmentioning

confidence: 99%

Rare-earths as catalytic centres in organo-inorganic polymeric frameworksElectronic supplementary information (ESI) available: selected bond angles and hydrogen interactions in 1, 2, 3; coordination environment of the two scandium atoms in 1; coordination modes of the three crystallographically independent carboxylate groups for 2 and 3. See http://www.rsc.org/suppdata/jm/b3/b314220e/

et al. 2004

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“…The reaction of alkenes with sulfide can proceed by either radical , or electrophilic additions . I investigated if the reaction of vinylsulfonic acid with sulfide in the presence of UV would lead to the production of 1-MES.…”

Section: Resultsmentioning

confidence: 99%

Identification and Biosynthesis of 1-Mercaptoethanesulfonic Acid (1-MES), an Analogue of Coenzyme M, Found Widely in the Methanogenic Archaea

White

2017

Biochemistry

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Here I report on the identification of 1-mercaptoethanesulfonic acid (1-MES), an analogue of 2-mercaptoethanesulfonic acid (coenzyme M, HSCoM). 1-MES and HSCoM were both present in the growth media of eight different methanogens at concentrations ranging from ∼1 to 100 μM. In an effort to determine a chemical origin of 1-MES, several plausible chemical routes were examined each assuming that HSCoM was the precursor. In all examined routes, no 1-MES was formed. However, 1-MES was formed when a solution of vinylsulfonic acid and sulfide were exposed to ultraviolet light. On the basis of these results, I conclude 1-MES is formed enzymatically. This was confirmed by growing a culture of Methanococcus maripaludis S2 in the presence of [1,1',2,2'-H]HSCoM and measuring the incorporation of deuterium into 1-MES. 1-MES incorporated three of the four deuteriums from the fed HSCoM. This result is consistent with the abstraction of a C-2 deuterium of the HSCoM, likely by a 5'-dAdoCH radical, followed by a radical rearrangement in which the sulfonic acid moves to position C-1, followed by abstraction of a H likely from 5'-dAdoCHD. At present, the reason for the production of 1-MES is not clear. This is the first report of the occurrence of 1-MES in Nature.

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“…The thiol‐ene and thiol‐Michael reactions emerged out of the question of why thiols undergo anti‐Markovnikovian addition under some conditions, and both reaction mechanisms were proposed by Kharash in the 1930s and 1940s, respectively 8, 9. Excellent early reviews were written well in advance of any identification of the unique common features of these reactions 10, 11…”

Section: Introductionmentioning

confidence: 99%

The emerging role of click reactions in chemical and biological engineering

Adzima

Bowman

2012

AIChE Journal

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The Thiylation of Olefins

Cited by 38 publications

References 2 publications

Identification and Biosynthesis of 1-Mercaptoethanesulfonic Acid (1-MES), an Analogue of Coenzyme M, Found Widely in the Methanogenic Archaea

The emerging role of click reactions in chemical and biological engineering

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