http://www.inchem.org/documents/jmpr/jmpmono/v84pr52.htm
LANCET
TOXIC EFFECTS OF DIAMINODIPHENYL-SULPHONE IN TREATMENT OF LEPROSY
ElizabethJ. Allday, M.B. Lond.
J. Barnes, M.D. N.U.I.
Published:August 04, 1951DOI:https://doi.org/10.1016/S0140-6736(51)91443-2
https://www.thelancet.com/journals/lancet/article/PIIS0140-6736(51)91443-2/fulltext
On the Electrolysis of Potassium Ethyl-Sulphone-Acetate
Published online by Cambridge University Press: 15 September 2014
Crum Brown and
Herbert W. Bolam
https://www.cambridge.org/core/journals/proceedings-of-the-royal-society-of-edinburgh/article/abs/div-classtitleon-the-electrolysis-of-potassium-ethyl-sulphone-acetatediv/50416D91CD0977A9AB8E55B2243D0445
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Organic Compounds of Sulphur, Selenium, and Tellurium: Volume 3
https://books.google.com/books?
id=enAoDwAAQBAJ&pg=PA357&lpg=PA357&dq=SULPHENE&source=bl&ots=BSe0yO5RTu&sig=ACfU3U1LgOn_G45mYV92DO_MbPB9JwU77g&hl=en&sa=X&ved=2ahUKEwjL27HPmo_yAhWRbc0KHa8tBWI4HhDoATAIegQIChAD#v=onepage&q=SULPHENE&f=false
Sulphone Treatment of Leprosy
Br Med J 1947; 1 doi: https://doi.org/10.1136/bmj.1.4509.798 (Published 07 June 1947)Cite this as: Br Med J 1947;1:798https://www.bmj.com/content/1/4509/798Density functional calculations show that the barrier to ring closure of ammonium betaines is significantly higher than the same process for sulfoniumbetaines,83 rationalizing the differing reactivity (and explaining why hydroxy ammonium salts are isolated from reactions of carbonyls and ammonium ylides at low temperature84).
Synthetic Reactions of M=C and M=N Bonds: Ylide Formation, Rearrangement, and 1,3-Dipolar Cycloaddition☆
J. Wang, Y. Zhang, in Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, 2013
[1,2]-Shift (Stevens Rearrangement) and Related Reactions
Ammonium ylides undergo [1,2]-shift in manner similar to oxonium and sulfonium ylides. A preferentially migrating group is usually a benzyl group. A sequence of intramolecular formation of ammonium ylide and subsequent rearrangement was extensively explored by West and co-workers in synthesis of cyclic amines.95 Rh2(OAc)4-catalyzed reaction of diazoketone 273 gave ammonium ylide 274, which undergoes [1,2]-shift to give piperidine derivatives 275 (eqn [40]).95 In this case, the migrating group is CH2C6H5, CO2Et and p-XC6H4. When X is MeO or Ac, homocoupling product 276 is also isolated in 19% or 25% yield, respectively. Formation of the homocoupling products is a strong evidence that the [1,2]-shift proceeds through a radical pair intermediate.18
https://www.sciencedirect.com/topics/chemistry/ammonium-ylide
Ylide Addition
Sometimes, nucleophiles adding to a carbonyl do not follow the normal reactivity patterns that have been common so far. This is often the case with the addition of ylides. Ylides are compounds that are often depicted with a positive charge one one atom and a negative charge on the next atom. They are examples of zwitterions, compounds that contain both positive and negative charges within the same molecule. What distinguishes them from other zwitterions is the proximity of the opposite charges.
The classic example of an ylide addition to a carbonyl is the Wittig reaction, which involves the addition of a phosphorus ylide to an aldehyde or ketone. Rather than producing an alcohol, the reaction produces and alkene. The reaction is driven by formation of a phosphorus oxide "side product".
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Reactions/Addition_Reactions/Addition_to_Carbonyls/Ylide_Addition
The classic example of an ylide addition to a carbonyl is the Wittig reaction, which involves the addition of a phosphorus ylide to an aldehyde or ketone. Rather than producing an alcohol, the reaction produces and alkene. The reaction is driven by formation of a phosphorus oxide "side product".
This is a special case. The phosphorus-oxygen bond is strong enough to change the course of this reaction away from the normal pattern, and it isn't something you would have been able to predict based on related reactions.
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Reactions/Addition_Reactions/Addition_to_Carbonyls/Ylide_Addition
Once the phosphonium salt has been made, the phosphorus ylide can then be obtained via deprotonation of a phosphonium ion. The hydrogens on a carbon next to a phosphorus cation are a little bit acidic because of the positive charge on the phosphorus. One of these hydrogens is easily removed via adddition of a very strong base such as sodium hydride.
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Reactions/Addition_Reactions/Addition_to_Carbonyls/Ylide_Addition
Show, with reaction arrows, formation of ylides from the three alkyltriphenyl phosphonium bromide salts shown above in Problem CO18.1.
The reaction of a phosphorus ylide with a carbonyl compound does begin like other nucleophilic additions. The ylide donates its nucleophilic lone pair to the carbonyl and the carbonyl pi bond breaks. However, the strong P-O bond then takes over the reaction. To begin, a lone pair on the resulting alkoxide ion is donated to the positively charged phosphonium ion.
Wait! That violates one of our mechanistic rules. Usually, we don't have an atom donate to a positively charged atom that already has an octet; if we do so, the atom will have too many electrons. However, the octet rule doesn't strictly apply to sulfur and phosphorus. These atoms are larger than second-row atoms like nitrogen and oxygen, and they are often observed to "exceed the octet rule". Sulfur and phosphorus are frequently observed with trigonal bipyramidal or octahedral molecular geometries, meaning they may have up to 12 electrons in their valence shells.
So go ahead! Donate a pair of electrons to the phosphorus. It can't help itself, because of the strength of the P-O bond that forms.
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Organic_Chemistry)/Reactions/Addition_Reactions/Addition_to_Carbonyls/Ylide_Addition
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