Bruce Lipshutz used Merrifield resin to scavenge this molecule and its tricky-to-separate oxidized derivative after reactions using Ni(0) (“nickel-zero”). Adding an acyl group to this molecule, rather than an ester, allows it to be cleaved during a reaction’s “traceless” variant. Four copies of this molecule are ligands on a tetrahedral complex that supplies palladium to cross-couplings. An excess of this molecule is separated alongside waste hydrazines in a reaction in which it prepares an alcohol for SN2 substitution after attacking the azo group of DIAD (“D-I-A-D”). This molecule is the bulkiest ligand on Wilkinson’s catalyst. This molecule lies at one corner of the square intermediate formed by a carbonyl and an ylide (“ILL-id”). This molecule is a key reagent in both the Mitsunobu and Wittig reactions. For 10 points, name this bulky compound with three aryl groups bound to phosphorus. ■END■
ANSWER: triphenylphosphine (“tri-phenyl-phosphine”) [accept Ph3PO, triphenylphosphine oxide, triphenylphosphonium ylide, or tetrakis(triphenylphosphine) palladium(0); prompt on TPPO by asking “what does that stand for?”]
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= Average correct buzz position