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Addition Reactions of a Phosphorus Triamide to Nitrosoarenes and Acylpyridines

Author(s)
te Grotenhuis, Colet; Mattos, Jared T.; Radosevich, Alexander T.
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Abstract
Tricoordinate phosphorus compounds react with a wide variety of double bonds through addition reactions. The dipolar and cyclic products formed are important intermediates in organophosphorus chemistry. We investigated the reactivity between phosphorus triamide 1 and nitrosoarenes and 2-acylpyridines. For sterically congested substrates, the formation of σ5,λ5-phosphorus products is observed. DFT calculations indicate this product is formed through a concerted [4 + 1] mechanism. For less sterically congested substrates, products are observed arising from cleavage of the N = O or C = O bond with formation of a terminal P = O bond and aryl nitrene or carbene migration into a P–N bond of the phosphorus triamide core. DFT calculations are consistent with an initial [2 + 1] addition to phosphorus followed by formal carbene/nitrene migration in these cases.
Date issued
2020-09
URI
https://hdl.handle.net/1721.1/127806
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Phosphorus, Sulfur, and Silicon and the Related Elements
Publisher
Taylor & Francis
Citation
te Grotenhuis, Colet et al. "Addition reactions of a phosphorus triamide to nitrosoarenes and acylpyridines." Phosphorus, Sulfur, and Silicon and the Related Elements (September 2020): 940-946
Version: Author's final manuscript
ISSN
1042-6507
1563-5325

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