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• W2955128511 abstract "Extensive DFT calculations provide deep mechanistic insights into the acylation reactions of tert-butyl dibenzo-7-phosphanobornadiene with PhCOX (X=Cl, Br, I, OTf) in CH2Cl2 solution. Such reactions are initialized by the nucleophilic P⋅⋅⋅C attack to the carbonyl group to form the acylphosphonium intermediate A+ together with X- anion, followed either by nucleophilic X-⋅⋅⋅P attack (X=Cl, Br, and I) toward A+ to eliminate anthracene or by slow rearrangement or decomposition of A+ (X=OTf). In contrast to the first case (X=Cl) that is rate-limited by the initial P⋅⋅⋅C attack, other reactions are rate-limited by the second X-⋅⋅⋅P attack for X=Br and I and even thermodynamically prevented for X=OTf, leading to isolable phosphonium salts. The rearrangement of phosphonium A+ is initiated by a P-C bond cleavage, followed either by sequential proton-shifts to form anthracenyl acylphosphonium or by deprotonation with additional base Et3N to form neutral anthracenyl acylphosphine. Our DFT results strongly support the separated acylphosphonium A+ as the key reaction intermediate that may be useful for the transfer of acylphosphenium in general." @default.
• W2955128511 created "2019-07-12" @default.
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• W2955128511 date "2019-06-01" @default.
• W2955128511 modified "2023-10-17" @default.
• W2955128511 title "Acylation Reactions of Dibenzo‐7‐phosphanorbornadiene: DFT Mechanistic Insights" @default.
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• W2955128511 doi "https://doi.org/10.1002/open.201900176" @default.
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