The Diverse Reactivity of an Al(I) Carbenoid Towards Phosphorus‐Based Ylides. The Crucial Role of Co‐Crystallised Lithium Halide

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Abstract
Attempts to generate NacNacAl‐based (NacNac=[ArNC(Me)CHC(Me)NAr]−; Ar=2,6‐iPr2C6H3) alkylidenes via reactions with trimethyl(methylidene), triphenyl(methylidene) and triethyl(ethylidene) phosphiranes led to new and unexpected reactivity patterns. Reaction with Me3P=CH2 resulted in the intermolecular deprotonation of the NacNac −CCH3 backbone. Reaction with Ph3P=CH2*LiI afforded an equimolar mixture of NacNacAlH2 and the ortho‐metalated adduct, NacNac'Al(η(C,C)2−CH2=PPh2(o‐C6H4)) (NacNac’=[ArNC(Me)CHC(=CH2)NAr]2−). Finally, the use of Et3P=CHMe*LiBr resulted in the fragmentation of the NacNac moiety.
Funding Information
  • Natural Sciences and Engineering Research Council of Canada (2017-05231, 2018-04255)

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