A Novel Three‐Component Reaction of Triphenylphosphine, DMAD, and Electron‐Deficient Styrenes: Facile Synthesis of Cyclopentenyl Phosphoranes.

Nair, Vijay; Deepthi, Ani; Beneesh, P. B.; Suresh, Eringathodi

doi:10.1002/chin.200636171

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“…The phosphorane (262) can be oxidized by a methanolic solution of cerium (IV) ammonium nitrate (CAN) in an oxygen atmosphere to (263). A mechanistic rationale for the formation of phosphorane (262) may be outlined as follows: Initially formed zwitterionic intermediate (3) from the reaction of (1) and (2) adds to the activated styrene (261) in a Michael fashion to yield a betaine (264); latter on cyclization and subsequent deprotonation can deliver the phosphorane (262) (Scheme 76) [218]. The reaction between benzoyl isothiocyanate (267) and (2) in the presence of (1) leads to dialkyl 2-(benzoylimino)-5-phenyl-4H-[1,3]dithiolo [4,5-b]pyrrole-4,6-dicarboxylates (268) with double insertion of the isothiocyanate, and dialkyl 2-phenyl-4-thioxo-4H-1,3-oxazine-5,6-dicarboxylates (269) (Scheme 77) [219].…”

Section: 5-dialkylmentioning

confidence: 99%

Preparation of Stabilized Phosphorus Ylides via Multicomponent Reactions and Their Synthetic Applications

Ramazani

Kazemizadeh

2011

COC

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Triphenylphosphine (TPP), dialkyl acetylenedicarboxylates (DAAD), and acids such as phenols, imides, amides, enols, oximes and alcohols react with each other via a multicomponent reaction to produce stabilized phosphorus ylides. The reactions take place easily, through formation of intermediate formed by the Michael addition of the triphenylphosphine to dialkyl acetylenedicarboxylates and concomitant protonation of the intermediate by an acid leads to vinyltriphenylphosphonium salts. The salts are unstable intermediates and undergo a subsequent Michael addition leads to stabilized phosphorus ylides. In some cases ylide products are stable, but in other cases they cannot be isolated and appear to occur as intermediates on the pathway to an observed product. The stabilized phosphorus ylides are able to take part in the normal intramolecular Wittig reactions and produce a variety of heterocyclic or carbocyclic compounds, but they are not able to participate in the intermolecular Wittig reactions.

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Section: 5-dialkylmentioning

confidence: 99%