Spencer C. Serin
University of British Columbia
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Featured researches published by Spencer C. Serin.
Angewandte Chemie | 2013
Paul W. Siu; Spencer C. Serin; Ivo Krummenacher; Thomas W. Hey; Derek P. Gates
The synthesis and study of main-group-element analogues of alkenes and alkynes containing genuine (p p)p bonds involving p-block elements is a central theme of inorganic chemistry. The prospect to “copy” the predictable and sophisticated reaction chemistry of C=C and C C bonds utilizing functional inorganic systems is particularly enticing. However, in many instances, the investigation of multiple bonds of heavy elements leads to fascinating, albeit unexpected, outcomes that reinforce the fundamental differences between the first and subsequent periods. Inspired by the intriguing analogy between P=C and C=C bonds in molecular chemistry, we developed the addition polymerization of phosphaalkenes as a route to new functional phosphorus-containing polymers (Scheme 1).
Chemistry: A European Journal | 2012
Julien Dugal-Tessier; Spencer C. Serin; Emmanuel B. Castillo-Contreras; Eamonn D. Conrad; Gregory R. Dake; Derek P. Gates
The design of a synthetic route to a class of enantiomerically pure phosphaalkene-oxazolines (PhAk-Ox) is presented. The condensation of a lithium silylphosphide and a ketone (the phospha-Peterson reaction) was used as the P=C bond-forming step. Attempted condensation of PhC(=O)Ox (Ox = CNOCH(iPr)CH(2)) and MesP(SiMe(3))Li gave the unusual heterocycle (MesP)(2)C(Ph)=CN-(S)-CH(iPr)CH(2)O (3). However, PhAk-Ox (S,E)-MesP=C(Ph)CMe(2)Ox (1 a) was successfully prepared by treating MesP(SiMe(3))Li with PhC(=O)CMe(2)Ox (52 %). To demonstrate the modularity and tunability of the phospha-Peterson synthesis several other phosphaalkene-oxazolines were prepared in an analogous manner to 1 a: TripP=C(Ph)CMe(2)Ox (1 b; Trip = 2,4,6-triisopropylphenyl), 2-iPrC(6)H(4)P=C(Ph)CMe(2)Ox (1 c), 2-tBuC(6)H(4)P=C(Ph)CMe(2)Ox (1 d), MesP=C(4-MeOC(6)H(4))CMe(2)Ox (1 e), MesP=C(Ph)C(CH(2))(4)Ox (1 f), and MesP=C(3,5-(CF(3))(2)C(6)H(3))C(CH(2))(4)Ox (1 g). To evaluate the PhAk-Ox compounds as prospective precursors to chiral phosphine polymers, monomer 1 a and styrene were subjected to radical-initiated copolymerization conditions to afford [{MesPC(Ph)(CMe(2)Ox)}(x){CH(2)CHPh}(y)](n) (9 a: x = 0.13n, y = 0.87n; GPC: M(w) = 7400 g mol(-1) , PDI = 1.15).
Inorganic Chemistry | 2016
Spencer C. Serin; Fraser S. Pick; Gregory R. Dake; Derek P. Gates
The synthesis of enantiomerically pure pyridine-bridged phosphaalkene-oxazolines ArP═C(Ph)(2,6-C5H3NOx) (1, Ar = Mes/Mes*, Ox = CNOCH(i-Pr)CH2/CNOCH(CH2Ph)CH2) is reported. This new ligand forms a κ(P), κ(2)(NN) dimeric complex with copper(I) (7) that dissociates into a cationic κ(3)(PNN) monomeric complex upon addition of a neutral ligand {[1a·CuL]OTf (8a-e): L = PPh3 (a), P(OPh)3 (b), 2,6-lutidine (c), 4-DMAP (d), 1-methylimidazole (e)}. The P-Cu bond lengths in 8 are influenced by the π-accepting/σ-donating properties of L, and this can be observed by changes in the δ(31)PP═C NMR shift. The donor-acceptor properties in complexes of type 8 have also been investigated by UV/vis spectroscopy and density functional theory calculations.
Chemical Society Reviews | 2016
Benjamin W. Rawe; Spencer C. Serin; Derek P. Gates
European Journal of Inorganic Chemistry | 2014
Paresh Kumar Majhi; Spencer C. Serin; Gregor Schnakenburg; Derek P. Gates; Rainer Streubel
Dalton Transactions | 2016
Spencer C. Serin; Gregory R. Dake; Derek P. Gates
Dalton Transactions | 2017
Khatera Hazin; Spencer C. Serin; Brian O. Patrick; Maria B. Ezhova; Derek P. Gates
Organometallics | 2014
Spencer C. Serin; Brian O. Patrick; Gregory R. Dake; Derek P. Gates
Macromolecules | 2016
Spencer C. Serin; Gregory R. Dake; Derek P. Gates
Dalton Transactions | 2017
Abhishek Koner; Spencer C. Serin; Gregor Schnakenburg; Brian O. Patrick; Derek P. Gates; Rainer Streubel