A New Reaction Pathway in Organophosphorus Chemistry: Competing SN2 and AE′ 
Pathways for Nucleophilic Attack at a Phosphorus–Carbon Cage Compound

Fish, Cheryl; Green, Michael; Kilby, Richard J.; Lynam, Jason M.; McGrady, John E.; Pantazis, Dimitrios A.; Russell, Christopher A.; Whitwood, Adrian C.; Willans, Charlotte E.

doi:10.1002/anie.200504546

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A New Reaction Pathway in Organophosphorus Chemistry: Competing S_N2 and AE′ Pathways for Nucleophilic Attack at a Phosphorus–Carbon Cage Compound

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Citation

Fish, C., Green, M., Kilby, R. J., Lynam, J. M., McGrady, J. E., Pantazis, D. A., et al. (2006). A New Reaction Pathway in Organophosphorus Chemistry: Competing S_N2 and AE′ Pathways for Nucleophilic Attack at a Phosphorus–Carbon Cage Compound. Angewandte Chemie International Edition, 45(22), 3628-3631. doi:10.1002/anie.200504546.

Cite as: https://hdl.handle.net/21.11116/0000-0007-3052-6

Abstract

Competition: A combination of ³¹P NMR spectroscopic and calculational studies have shown that nucleophilic substitution in the phosphorus–carbon cage compound ClP₃(CtBu)₂ occurs through competing S_N2‐ and AE′‐type reaction pathways (see scheme for model compound ClP₃(CH)₂). The AE′ mechanism results in the formation of a C_2v‐symmetric intermediate prior to release of the chloride ion.