CHLORINATION OF β,β-DICHLORO-ETHYL SULFIDE. II<sup>1</sup>

Dawson, T. P.; Lawson, W. E.

doi:10.1021/ja01411a021

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“…Flury (20) advanced the theory that the vesicant action was due to the reactivity of the sulfur atom, but when it was found that the sulfoxide containing quadrivalent sulfur was non-vesicant it lost much of its probability. The idea that the unlooked-for reaction of bis (/3-chloroethyl) sulfide with sodium alcohólate to give the highly toxic divinyl sulfide (5,29) might have a bearing on the vesicant action was discounted by the later investigations of Bales and Nickelson (6), who found that the yield of divinyl sulfide decreases markedly when the per cent of alcohol drops below 80, and of Lawson and Dawson (38) who obtained no trace of divinyl sulfide from bis (/3-chloroethyl) sulfide when using secondary sodium phosphate and sodium carbonate in 50 per cent alcohol, which substance gives hydrogenion concentrations approaching those in body tissues.…”

Section: Ch2c1mentioning

confidence: 99%

β,β' Dichloroethyl Sulfide (Mustard Gas).

Jackson¹

1934

Chem. Rev.

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Section: Ch2c1mentioning

confidence: 99%

β,β' Dichloroethyl Sulfide (Mustard Gas).

Jackson¹

1934

Chem. Rev.

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The P ummerer Reaction of Sulfinyl Compounds

Lucchi

Miotti²,

Modena³

1991

Organic Reactions

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The Pummerer reaction involves the formation of an α‐functionalized sulfide from a sulfoxide bearing at least one α‐hydrogen atom. The reaction can also be described as an internal redox process where the SX group is reduced and the α carbon is oxidized. The first report by Pummerer on the reaction which now bears his name appeared in 1909 and described the formation of thiophenol and glyoxylic acid on heating phenylsulfinylacetic acid with mineral acids. The products Pummerer observed resulted from hydrolysis of the initially formed α‐substituted sulfides, which are the typical products of the reaction. The term “Pummerer reaction” was later extended to the reaction of sulfoxides with acid anhydrides. Selenium and nitrogen analogs undergo similar reactions. The former is known as the seleno–Pummerer reaction, and the latter is usually referred to as the Polonovski reaction. The sila–Pummerer reaction, which is also discussed in this chapter, is the rearrangement of sulfoxides bearing a silyl group on the α carbon. From a mechanistic point of view there are many other reactions, sometimes given specific names, such as the Sommelet–Hauser, Stevens, and Vilsmeier rearrangements, that appear to resemble the Pummerer reaction. Reactions in which the sulfoxide group acts as an oxidant in an intermolecular redox process have characteristics similar to the typical Pummerer reaction. The α‐halogenation of sulfides, in which the sulfide sulfur may first be oxidized to a halosulfonium salt that rearranges to the final product, is formally similar to the Pummerer reaction. For the sake of clarity and to be as exhaustive as possible, we have limited the scope of this chapter to the restrictive definition.

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CHLORINATION OF β,β-DICHLORO-ETHYL SULFIDE. II¹

Abstract: of /3,/3-dichloro-ethyl sulfide, ii 3125 4. A number of the chlorinated and brominated products from ß,ßdichloro-ethyl sulfide together with some of their derivatives have been prepared.Wilmington, Delaware

Cited by 2 publications

References 0 publications

β,β' Dichloroethyl Sulfide (Mustard Gas).

β,β' Dichloroethyl Sulfide (Mustard Gas).

The P ummerer Reaction of Sulfinyl Compounds

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CHLORINATION OF β,β-DICHLORO-ETHYL SULFIDE. II1

Abstract: of /3,/3-dichloro-ethyl sulfide, ii 3125 4. A number of the chlorinated and brominated products from ß,ßdichloro-ethyl sulfide together with some of their derivatives have been prepared.Wilmington, Delaware

Cited by 2 publications

References 0 publications

β,β' Dichloroethyl Sulfide (Mustard Gas).

β,β' Dichloroethyl Sulfide (Mustard Gas).

The P ummerer Reaction of Sulfinyl Compounds

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CHLORINATION OF β,β-DICHLORO-ETHYL SULFIDE. II¹