Abstract:trans,trans-1,4-Diphenylbuta-1,3-diene reacts with elemental (red) phosphorus in the superbasic KOH / DMSO (H2O) system (120°C, 3 h) to give, after acidic work-up, 1,4-diphenylbutylphosphinic acid in 48% yield.
Citation:
A. V. Artem'ev, A. O. Sutyrina, E. A. Matveeva, A. I. Albanov, L. V. Klyba, “Unexpected formation of 1,4-diphenylbutylphosphinic acid from 1,4-diphenylbuta-1,3-diene and elemental phosphorus via the Trofimov–Gusarova reaction”, Mendeleev Commun., 27:2 (2017), 137–138
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This publication is cited in the following 7 articles:
Vladimir A. Kuimov, Svetlana F. Malysheva, Natalia A. Belogorlova, Ruslan I. Fattakhov, Alexander I. Albanov, Irina Yu. Bagryanskaya, Nikolay I. Tikhonov, Boris A. Trofimov, “Straightforward Superbase-Mediated Reductive O-Phosphorylation of Aromatic and Heteroaromatic Ketones with Red Phosphorus in the Superbase Suspension KOH/DMSO(H2O)”, Molecules, 30:6 (2025), 1367
Vladimir A. Kuimov, Svetlana F. Malysheva, Natalia A. Belogorlova, Nina K. Gusarova, Boris A. Trofimov, “Chemoselective synthesis of long-chain alkyl-H-phosphinic acids via one-pot alkylation/oxidation of red phosphorus with alkyl-PEGs as recyclable micellar catalysts”, Org. Biomol. Chem., 19:48 (2021), 10587
N. K. Gusarova, B. A. Trofimov, “Organophosphorus chemistry based on elemental phosphorus: advances and horizons”, Russian Chem. Reviews, 89:2 (2020), 225–249
Svetlana F. Malysheva, Vladimir A. Kuimov, Natalia A. Belogorlova, Alexander I. Albanov, Nina K. Gusarova, Boris A. Trofimov, “Superbase‐Assisted Selective Synthesis of Triarylphosphines from Aryl Halides and Red Phosphorus: Three Consecutive Different SNAr Reactions in One Pot”, Eur J Org Chem, 2019:36 (2019), 6240
Lie Wu, Shi Bian, Hao Huang, Jiahong Wang, Danni Liu, Paul K. Chu, Xue-Feng Yu, “Black Phosphorus: An Effective Feedstock for the Synthesis of Phosphorus-Based Chemicals”, CCS Chem, 1:2 (2019), 166
N. K. Gusarova, A. O. Sutyrina, V. A. Kuimov, S. F. Malysheva, N. A. Belogorlova, P. A. Volkov, B. A. Trofimov, “Single-stage synthesis of alkyl-H-phosphinic acids from elemental phosphorus and alkyl bromides”, Mendeleev Commun., 29:3 (2019), 328–330
S. F. Malysheva, V. A. Kuimov, A. B. Trofimov, N. A. Belogorlova, Yu. I. Litvintsev, A. M. Belogolova, N. K. Gusarova, B. A. Trofimov, “2-Halopyridines in the triple reaction in the Pn/KOH/DMSO system to form tri(2-pyridyl)phosphine: Experimental and quantum-chemical dissimilarities”, Mendeleev Commun., 28:5 (2018), 472–474
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