78076-18-3Relevant academic research and scientific papers
VERSATILITE DE REACTIVITE DE L'ACETYLENE DICARBALDEHYDE ET DES ALDEHYDES α-ACETYLENIQUES A L'EGARD DES DIENES CONJUGUES CYCLIQUES ET HETEROCYCLIQUES EN MILIEU ACIDE
Gorgues, A.,Simon, A.,Coq, A. Le,Hercouet, A.,Corre, F.
, p. 351 - 370 (1986)
The preparation of acetylenedicarbaldehyde 1 and the corresponding mono acetal 2 is described.A comparison of their reactivity with other α-acetylenic aldehydes RCCCHO 3 to 9 towards conjugated cyclic or heterocyclic dienes is presented.Under neutral conditions, the only expected Diels-Alder adducts I are formed.Under acidic conditions (HCO2H, CF3CO2H or eventually AcOH) they afford the only Diels-Alder adduct I when the cyclodiene does not present any aromatic character, and, on the opposite case, the Michael adducts II with more or less important amounts of I; starting from furan, a third pathway could also be observed dealing with t he formation of the double electrophilic substitution compounds III.The mechanisms are discussed and particularly, a common dipolar intermediate P is suggested to account for the competitive formation of I and II.
Versatilite de la reactivite de l'acetilenedicarbaldehyde et d'aldehydes α-acetileniques a l'egard des dienes conjugues cycliques et heterocycliques en milieu acide.
Gorgues, Alain,Simon, Andre,le Coq, Andre,Corre, Francois
, p. 625 - 628 (2007/10/02)
Formic solutions of ADCA react with cyclic and heterocyclic conjugated dienes affording the Diels-Alder 1 or pseudo-Michael 2 adducts depending on the nature of the diene.Generalisation to R-CC-CHO and furan shows a similar behaviour (R=CO2E
