Formyl onium salts: synthesis and decomposition pathways

Weiß, Robert; Roth, Reinhard

doi:10.1039/c39870000317

Cited by 14 publications

(2 citation statements)

References 2 publications

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“…We found that imidazoles 1a , b react readily with bis(diisopropylamino)phosphenium triflate 4b affording imidazolium triflates 5a , b in high yields (Scheme ). Structures 5a , b are crystalline, high-melting compounds, insoluble in ether.…”

Section: Resultsmentioning

confidence: 99%

N-Phosphorylated Imidazolium Salts as Precursors to 2- and 5-Phosphorylated Imidazoles and New Imidazol-2-ylidenes Featuring the PNCN Unit

et al. 2010

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It has been experimentally proven that the reaction of 1- or 1,2-disubstituted imidazoles with diorganylphosphorus(III) halides proceeds via initial formation of N-phosporylated imidazolium salts. Treatment of these salts with strong bases results in phosphorylation of the parent imidazoles at the 2- or 5-positions, correspondingly. In a previous case, imidazol-2-ylidenes are formed as intermediates. With both N1 and N3 atoms bearing sterically demanding or/and π-donating groups, deprotonation of 1,3-disubstituted imidazolium salts with NaN(SiMe(3))(2) afforded new stable N-phosphorus-substituted Arduengo-type carbenes.

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Section: Resultsmentioning

confidence: 99%

N-Phosphorylated Imidazolium Salts as Precursors to 2- and 5-Phosphorylated Imidazoles and New Imidazol-2-ylidenes Featuring the PNCN Unit

et al. 2010

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“…We have synthesized the latter compound in previous work. [4] Above 80°C, it decomposes into L, HOTf, and CO. In any case, both of these mechanistic variations of the deformylation process would profit from the pronounced tendency of 5 to act as a "carbanionic" leaving group.…”

Section: Resultsmentioning

confidence: 99%

Massive Electrostatic Effects on Heteropolar C–C Disconnections: Transforming a Phenyl Anion into a Potent Leaving Group

2005

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The SASAPOS protocol – a general reaction sequence which allows the complete exchange of various neutral ligands X in organic, elementorganic, and inorganic systems by cationic ligands L+ – has been applied to a small variety of pentafluoro benzene derivatives C6F5–E (E = –C(O)H, –C(N–Ph)H, –PCl2/–P(L+)2, –H) yielding the ion clusters C6(L+)5–E (F3CSO3–)5. The reaction conditions required to observe a heteropolar C–C or C–P disconnection, with a highly stabilized pentakisonio‐substituted phenyl anion as the key intermediate, are specified. When E = H, the latter compound also figures as the key intermediate during H/D exchange under basic conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Elektrostatische Aktivierung hypervalenter Organoiodverbindungen: Bis(onio)‐substituierte Aryliod(III)‐Salze

Weiß¹,

Seubert²

1994

Angewandte Chemie

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Formyl onium salts: synthesis and decomposition pathways

Abstract: lsolable formyl-pyridinium and -imidazolium salts are generated by treating Lewis acid-base pairs of type Me3SiA-N-heterocycle ( A = leaving group) with acetic formic anhydride; their thermal and base-catalysed decarbonylation is discussed in the light of theoretical data.

Cited by 14 publications

References 2 publications

N-Phosphorylated Imidazolium Salts as Precursors to 2- and 5-Phosphorylated Imidazoles and New Imidazol-2-ylidenes Featuring the PNCN Unit

N-Phosphorylated Imidazolium Salts as Precursors to 2- and 5-Phosphorylated Imidazoles and New Imidazol-2-ylidenes Featuring the PNCN Unit

Massive Electrostatic Effects on Heteropolar C–C Disconnections: Transforming a Phenyl Anion into a Potent Leaving Group

Elektrostatische Aktivierung hypervalenter Organoiodverbindungen: Bis(onio)‐substituierte Aryliod(III)‐Salze

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