An Efficient Route to New 1,2,4,3-Triazaphosphole-3-Oxide Derivatives

Smadhi, Meriem; Abderrahim, Raoudha

doi:10.1080/10426500903567521

Cited by 9 publications

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“…Only a handful of references to triazaphospholenes are known to us, and no examples are employed in catalysis . We envisioned formation of triazaphospholenes by the reaction of an amidrazone with a phosphorus trihalide in the presence of an acid scavenger.…”

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“…Regardless of this result, the syntheses of 2a , 3 , and 4 establish spectroscopic parameters for observing more reactive triazaphospholenes by NMR. Accordingly, we prepared several less hindered amidrazones. ,, These were subsequently converted to the corresponding triazaphospholene halides ( 2b – 2h , Figure ) by cyclization with a phosphorus trihalide in the presence of triethylamine. Unfortunately, attempts to convert these compounds to benzyloxides did not give clean product mixtures.…”

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Hydroboration Catalyzed by 1,2,4,3-Triazaphospholenes

et al. 2017

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The synthesis and study of the catalytic activity of 1,2,4,3-triazaphospholenes (TAPs) is reported. TAPs represent a more modular scaffold than previously reported diazaphospholenes. TAP halides were shown to catalyze the 1,2 hydroboration of 19 imines, and three α,β unsaturated aldehydes with pinacolborane, including examples that did not undergo hydroboration by previously reported diazaphospholene systems. DFT calculations support a mechanism where a triazaphospholene cation interacts with the substrate, a mechanism distinct from diazaphospholene catalyzed hydroborations.

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