Novel diphenylphosphine derivatives of 2,2′-bithiophene, 2,2′:5′,2″-terthiophene, 2-(2′-thienyl)pyridine and 2,6-di-2′-thienylpyridine. Crystal structures of 5,5′-bis(diphenylphosphino)-2,2′-bithiophene, diphenyl{5-[6′-(diphenylphosphino)-2′-pyridyl]-2-thienyl}phosphine and 2,6-bis[5′-(diphenylphosphino)-2′-thienyl]pyridine

We report the synthesis and characterisation of eight molecules that have in common a diphenylphosphino group bonded to an α-carbon atom of a thienyl or pyridyl ring: 5,5′-bis(diphenylphosphino)-2,2′-bithiophene1; diphenyl(2,2′-bithienyl-5-yl)phosphine2; 5,5″-bis(diphenylphosphino)-2,2′:5′,2″-terthiophene 3; diphenyl(2,2′:5′,2″-terthienyl-5-yl)phosphine 4; diphenyl phosphine 5; diphenyl phosphine 6; diphenyl{5- -2-thienyl}phosphine 7; and 2,6-bis pyridine 8

2002

Scholarcy highlights

  • We report the synthesis and characterisation of eight molecules that have in common a diphenylphosphino group bonded to an α-carbon atom of a thienyl or pyridyl ring: 5,5′-bis(diphenylphosphino)-2,2′-bithiophene; diphenyl(2,2′-bithienyl-5-yl)phosphine2; 5,5″-bis(diphenylphosphino)-2,2′:5′,2″-terthiophene 3; diphenyl(2,2′:5′,2″-terthienyl-5-yl)phosphine 4; diphenylphosphine 5; diphenylphosphine 6; diphenyl{5--2-thienyl}phosphine 7; and 2,6-bispyridine 8
  • Methods used for their synthesis range from lithiation of the parent heterocycle and subsequent reaction with PPh2Cl to the use of coupling reactions catalysed by metal complexes to assemble the molecule from its subunits
  • The crystal and molecular structures of 1, 7 and 8 have been determined and show that the 2,2′-bithienyl moiety in 1 adopts an s-trans-conformation, while the 2-(2′-thienyl)pyridyl moieties in 7 and 8 adopt s-cis-conformations in the solid state. These compounds represent a new series of ligands that are expected to bond to metals through the phosphorus and/or nitrogen atoms rather than a sulfur atom, in view of the poor donor ability of a thiophene sulfur towards metals
  • Reproduced material should be attributed as follows: For reproduction of material from NJC: - Reproduced by permission of The Royal Society of Chemistry on behalf of the Centre National de la Recherche Scientifique and the RSC
  • For reproduction of material from PPS: - Reproduced by permission of The Royal Society of Chemistry on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC
  • For reproduction of material from all other RSC journals: - Reproduced by permission of The Royal Society of Chemistry

Need more features? Save interactive summary cards to your Scholarcy Library.