Collect. Czech. Chem. Commun. 2010, 75, 785-805
Published online 2010-08-09 09:39:50

Theoretical study and synthesis of the reaction between triphenylphosphine, dialkyl acetylenedicarboxylates and 2-aminobenzimidazole, 2-hydroxy-3-nitropyridine or 1,2,3,4-tetrahydrocarbazole

Sayyed Mostafa Habibi-Khorassania,*, Malek Taher Maghsoodloua, Ali Ebrahimia, Reza Heydaria, Nourollah Hazeria, Mohammad Amin Kazemiana, Mahmoud Nassirib, Belghais Adroma and Mohammad Zakarianejada

a Department of Chemistry, The University of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran
b Department of Maritime, The University of Chabahar, Chabahar, Iran


Triphenylphosphine reacts with dialkyl acetylenedicarboxylates in the presence of heterocyclic compounds, such as 2-aminobenzimidazole, 2-hydroxy-3-nitropyridine or 1,2,3,4-tetrahydrocarbazole to generate stable phosphorus ylides. Some ylides exist in solution as a mixture of two geometrical isomers as a result of restricted rotation around the carbon–carbon partical double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group, whereas others occur as a single isomer only. For this reason, the assignments of more stable Z- or E-isomers as the major or minor forms were investigated using theoretical calculations.

Keywords: Heterocyclic compounds; Stable phosphorus ylides; Theoretical calculations.

References: 46 live references.