08-01-2021-0317 - The anions resulting from dissolving potassium in HMPT are also suitable for generating reactive ylides from their corresponding salts, HMPT also turning out to be a favorable solvent for many ylide reactions (equation 12).61

The anions resulting from dissolving potassium in HMPT are also suitable for generating reactive ylides from their corresponding salts, HMPT also turning out to be a favorable solvent for many ylide reactions (equation 12).61

https://www.sciencedirect.com/topics/chemistry/phosphonium-ylide


Many alkoxides (especially sodium methoxide, sodium ethoxide, [radioactive] potassium t-butoxide [derivs/etc.] and others) can be used as bases in ylide syntheses (equation 13).35 The reaction is carried out in the corresponding alcohol or another inert solvent [air]. The alkoxide method has some advantages: alkoxide bases are easy to handle, ylide generation may be effected in a homogeneous phase and phosphonium salts carrying corresponding alkoxycarbonyl groups are not cleaved at the alkoxy function.
https://www.sciencedirect.com/topics/chemistry/phosphonium-ylide

The anions resulting from dissolving potassium in HMPT are also suitable for generating reactive ylides from their corresponding salts, HMPT also turning out to be a favorable solvent for many ylide reactions (equation 12).61
(12)

Apart from the bases mentioned a series of other nitrogen bases (ammonia, triethylamine, pyridine, cyclic amidines, lithium diethylamide, lithium diisopropylamide, lithium piperidide, etc.) have been used to deprotonate phosphonium salts.

Many alkoxides (especially sodium methoxide, sodium ethoxide, potassium t-butoxide and others) can be used as bases in ylide syntheses (equation 13).35 The reaction is carried out in the corresponding alcohol or another inert solvent.

https://www.sciencedirect.com/topics/chemistry/phosphonium-ylide
Synthesis: Carbon With No Attached Heteroatoms

P. Savignac, ... M. Savignac, in Comprehensive Organic Functional Group Transformations II, 2005
1.16.1.1 Alkenation via the Wittig Reaction

The Wittig reaction is the reaction of phosphonium ylideswith carbonyl compounds leading to the formation of alkenesand phosphine oxides by transfer of an alkylidene group to a carbonyl compound with displacement of the carbonyl oxygen. It was discovered in 1953 when Wittig and Geissler treated methyltriphenylphosphonium iodide 1 with phenyllithium and obtained triphenylphosphonium methylide 2, which, in reaction with benzophenone, gave 1,1-diphenylethylene 3 and triphenylphosphine oxide (Scheme 1) <1953LA44>.

https://www.sciencedirect.com/topics/chemistry/phosphonium-ylide

Discussion of the use of polymer-supported reagents, and preparations and uses of carbodiphosphoranes and phosphacumulenes bring this venerable topic up to date.

https://www.sciencedirect.com/topics/chemistry/phosphonium-ylide

Phosphonium salts may also be converted to ylides by electrochemical procedures80,83 The preparative applicability of these methods, however, seems to be limited.

https://www.sciencedirect.com/topics/chemistry/phosphonium-ylide
Corey-Chaykovsky Reaction

The reaction of sulfur ylides with carbonyl compounds such as ketones or the related imines leads to the corresponding epoxides or aziridines.

https://www.organic-chemistry.org/namedreactions/corey-chaykovsky-reaction.shtm

USEPA
Health & Environmental Research Online (HERO)

HERO ID
928080
Reference Type
Journal Article

Title
Four-coordinate and pseudo five-coordinate Hg(II) complexes of a new bidentate phosphorus ylide: X-ray crystal structure and spectral characterization
Author(s)
Sabounchei, SJ; Samiee, S; Salehzadeh, S; Nojini, ZB; Irran, E

Year
2010

Is Peer Reviewed?
Yes

Journal
Journal of Organometallic Chemistry
ISSN: 0022-328X
EISSN: 1872-8561

Volume
695
Issue
10-11
Page Numbers
1441-1450

DOI
10.1016/j.jorganchem.2010.02.029
Web of Science Id
WOS:000277652500002
URL
http://linkinghub.elsevier.com/retrieve/pii/S0022328X1000121X

https://hero.epa.gov/hero/index.cfm/reference/details/reference_id/928080