Oxo-phospholes from the alkoxyphosphonium ylides formed in the reaction of trialkyl phosphites or dialkyl phosphonites with dimethyl acetylenedicarboxylate

1988 ◽  
pp. 175 ◽  
Author(s):  
Julian C. Caesar ◽  
D. Vaughan Griffiths ◽  
John C. Tebby
Keyword(s):  
Dimethyl Acetylenedicarboxylate ◽  
Trialkyl Phosphites

Synthesis of Functionalised Phosphonates or Phosphoranes by Reaction between Trialkyl Phosphites or Triphenylphosphine, Dimethyl Acetylenedicarboxylate and Aldehyde Ethyl Carbazones

2009 ◽  
Vol 2009 (5) ◽  
pp. 329-332 ◽  
Author(s):  
Mohammad Anary-Abbasinejad ◽  
Mohammad H. Mosslemin ◽  
Alireza Hassanabadi ◽  
Alimohammad Dehghan
Keyword(s):  
Phosphonium Salt ◽  
Aromatic Aldehydes ◽  
Conjugate Addition ◽  
Dimethyl Acetylenedicarboxylate ◽  
Reactive Intermediate ◽  
Trialkyl Phosphites

Protonation of the reactive intermediate produced from the reaction between trialkyl phosphites and dimethyl acetylenedicarboxylate by ethyl carbazones of aromatic aldehydes following by conjugate addition of the anion of ethyl carbazone on the phosphonium salt intermediate leads to functionalised phosphonates in good yields. Triphenylphosphine also reacted with dimethyl acetylenedicarboxylate and ethyl carbazones to produce functionalised phosphoranes in good yields.

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