Nachweis von Alkylidenoxophosphoranen durch Cycloaddition mit Carbonylverbindungen

Regitz, Manfred; Scherer, Hans; Illger, Walter; Eckes, Helnut

doi:10.1002/ange.19730852416

Cited by 17 publications

(1 citation statement)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The annulation of diazo(phenyl)methyl-(diphenyl)phospine oxide with aromatic aldehydes was first conducted in benzene under UV photo irradiation. The desired annuladducts were first identified as four-membered 1,2-oxaphosphetane 2-oxides 77,78 and further corrected as benzo[d] [1,2]oxaphosphinine 2-oxides, 79 accompanied by the aldehydeinserted products and the cyclopropanation products of the solvent benzene with in situ generated phosphorylcarbene intermediates before the Wolff rearrangement (Scheme 54).…”

Section: -(Ethoxy(hydroxy)phosphoryl)benzoic Acid Underwent the [4+2]mentioning

confidence: 99%

Synthesis of 1,2-oxaphosphinane 2-oxides and 1,2-oxaphosphinine 2-oxides: δ-phosphonolactones and δ-phosphinolactones

2023

New J. Chem.

View full text Add to dashboard Cite

show abstract

Section: -(Ethoxy(hydroxy)phosphoryl)benzoic Acid Underwent the [4+2]mentioning

confidence: 99%

Synthesis of 1,2-oxaphosphinane 2-oxides and 1,2-oxaphosphinine 2-oxides: δ-phosphonolactones and δ-phosphinolactones

2023

New J. Chem.

View full text Add to dashboard Cite

show abstract

Chemie der Phosphorylcarbene

Regitz

1975

Angewandte Chemie

View full text Add to dashboard Cite

Phosphorylcarbene sind erst in den letzten Jahren bei synthetischen Versuchen auf dem Gebiet der Phosphoryldiazoalkane bekannt geworden. Ihr praparativer Wert besteht zum einen in der Einfiihrung von Phosphorylgruppen in organische Verbindungen, etwa bei der Phosphorylcyclopropanierung von Alkenen oder Arenen und der Phosphorylcyclopropenierung von Alkinen; zum anderen gehen die Phosphorylcarbene leicht Umlagerungen ein: Hydrid-, Alkyl-, Aryl-und Acylverschiebungen fuhren zu phosphorylierten Alkenen. Die Phosphorylcarben/Methylenphosphanoxid-Umlagerung macht die kurzlebigen P-Analoga der Ketene zuganglich. Die Vinylcarben/Allen-Umlagerung schlierjlich wurde erst in diesem Zusammenhang entdeckt: sie konkurriert mit dem RingschluR zum Cyclopropen.

show abstract

Chemistry of Phosphorylcarbenes

Regits

1975

Angew. Chem. Int. Ed. Engl.

View full text Add to dashboard Cite

Phosphorylcarbenes, which have become known only recently during synthetic experiments in the field of phosphoryldiazoalkanes, have twofold preparative value. In the first place, they can be used to introduce phosphoryl groups into organic compounds, as in the phosphoryl‐cyclopropanation of alkenes or arenes and in the phosphorylcyclopropenation of alkynes. Secondly, phosphorylcarbenes readily undergo rearrangements; hydride, alkyl, aryl, or acyl shifts lead to phosphorylated alkenes. The phosphorylcarbene/methylenephosphane oxide rearrangement provides access to the short‐lived P analogs of the ketenes. Finally, the vinylcarbene/allene rearrangement was first discovered in this connection; it competes with ring closure to the cyclopropene.

show abstract

Nachweis von Alkylidenoxophosphoranen durch Cycloaddition mit Carbonylverbindungen

Cited by 17 publications

References 4 publications

Synthesis of 1,2-oxaphosphinane 2-oxides and 1,2-oxaphosphinine 2-oxides: δ-phosphonolactones and δ-phosphinolactones

Synthesis of 1,2-oxaphosphinane 2-oxides and 1,2-oxaphosphinine 2-oxides: δ-phosphonolactones and δ-phosphinolactones

Chemie der Phosphorylcarbene

Chemistry of Phosphorylcarbenes

Contact Info

Product

Resources

About