Abstract
Reactions of benzyl potassium species with CO are shown to proceed via transient carbene‐like intermediates that can undergo either dimerization or further CO propagation. In a sterically unhindered case, formal dimerization of the carbene is the dominant reaction pathway, as evidenced by the isolation of ((Ph3SiO)(PhCH2)C)2 2 and PhCH2C(O)CH(OH)CH2Ph 3. Reactions with increasingly sterically encumbered reagents show competitive reaction pathways involving intermolecular dimerization leading to species analogous to 2 and 3 and those containing newly‐formed five‐membered rings tBu2C6H2(C(OSiR3)C(OSiR3)CH2) (R=Me 6, Ph 7). Even further encumbered reagents proceed to either dimerize or react with additional CO to give a ketene‐like intermediates, thus affording a 7‐membered tropolone derivative 14 or the dione (3,5‐tBu2C6H3)3C6H2CH2C(O))2 15.
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