Thermal rearrangement of thiocarbonyl-stabilised triphenylphosphonium ylides leading to (Z)-1-diphenylphosphino-2-(phenylsulfenyl)alkenes and their coordination chemistry
Abstract
While thiocarbonyl-stabilised phosphonium ylides generally react upon flash vacuum pyrolysis by extrusion of Ph3PS to give alkynes in an analogous way to their carbonyl-stabilised analogues, two examples with a hydrogen atom on the ylidic carbon are found to undergo a quite different process. The net transfer of a phenyl group from P to S gives (Z)-configured 1-diphenylphosphino-2-(phenylsulfenyl)alkenes in a novel isomerisation process via intermediate λ5-1,2-thiaphosphetes. These prove to be versatile hemilabile ligands with a total of seven complexes prepared involving five different transition metals. Four of these have been characterised by X-ray diffraction with two involving the bidentate ligand forming a five-membered ring metallacycle and two with the ligand coordinating to the metal only through phosphorus.
Citation
Aitken , R A , Dawson , G , Keddie , N S , Kraus , H , Milton , H L , Slawin , A M Z , Wheatley , J & Woollins , J D 2023 , ' Thermal rearrangement of thiocarbonyl-stabilised triphenylphosphonium ylides leading to ( Z )-1-diphenylphosphino-2-(phenylsulfenyl)alkenes and their coordination chemistry ' , Molecules , vol. 29 , no. 1 , 221 . https://doi.org/10.3390/molecules29010221
Publication
Molecules
Status
Peer reviewed
ISSN
1420-3049Type
Journal article
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