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2 article(s) from Lozovskiy, Stanislav V.

Different reactivity of phosphorylallenes under the action of Brønsted or Lewis acids: a crucial role of involvement of the P=O group in intra- or intermolecular interactions at the formation of cationic intermediates

Stanislav V. Lozovskiy,
Alexander Yu. Ivanov and
Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2019, 15, 1491–1504, doi:10.3762/bjoc.15.151

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Figure 1: Allenes 1a–j used in this study.

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Scheme 1: Transformations of allene 1g in TfOH leading to the formation of cations E1, E2 and E4 including se...

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Figure 2: ³¹P NMR monitoring of the progress of transformation of E1 into E2 and E4 in TfOH at room temperatu...

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Scheme 2: Results of the hydrolysis of cations A–H.

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Scheme 3: Preparation of amides 6a,b from cations A, B, and F–H.

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Scheme 4: Large-scale one-pot solvent-free synthesis of amides 6a,b from the corresponding propargylic alcoho...

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Scheme 5: AlCl₃-promoted hydroarylation of allene 1b by benzene leading to alkene Z-11n.

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Scheme 6: Reaction of allene 1a with benzene under the action of AlCl₃ followed by quenching of the reaction ...

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Scheme 7: Multigram-scale one-pot synthesis of indane 12d from 2-methylbut-3-yn-2-ol.

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Figure 3: NMR spectra of starting allene 1a (black) and its complex with 1 equivalent of AlCl₃ 13 (red) in CD₂...

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Scheme 8: ¹H, ¹³C, and ³¹P NMR monitoring of AlCl₃-promoted reactions of allene 1a leading to compounds E-14 ...

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Scheme 9: Plausible reaction mechanism A for the formation of compounds 9, 10, 11, 12 from aillene 1a involvi...

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Scheme 10: Plausible reaction mechanism B of formation of compounds 11, 12 from allene 1a involving HCl–AlCl₃ ...

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Figure 4: Visualization of LUMO, only positive values are shown, isosurface value 0.043: (a) species 16, (b) ...

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Published 08 Jul 2019

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Generation of 1,2-oxathiolium ions from (arysulfonyl)- and (arylsulfinyl)allenes in Brønsted acids. NMR and DFT study of these cations and their reactions

Stanislav V. Lozovskiy,
Alexander Yu. Ivanov,
Olesya V. Khoroshilova and
Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2018, 14, 2897–2906, doi:10.3762/bjoc.14.268

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Scheme 1: (Arylsulfinyl)allenes 1 and (arylsulfonyl)allenes 2 used in this study.

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Figure 1: X-ray crystal structures of compounds 2h (CCDC 1843276), 3e (CCDC 1843277), 5c (CCDC 1580895), 7b (...

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Scheme 2: Plausible reaction mechanisms of transformations of allene 2a in Brønsted acids.

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Scheme 3: Selective formation of butadienes 3a–h from allenes 2a–h.

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Scheme 4: Reactions of allenes 2 in the system HFIP/TfOH followed by interaction with nucleophiles leading to...

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Scheme 5: Formation of thiochromene 1,1-dioxides 5a–c from allenes 2a,c,d.

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Scheme 6: Formation of (arylsulfonyl)acetones 6a,b from allenes 2h,j in TfOH (100 °C, 0.5 h) followed by hydr...

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Scheme 7: Reactions of (arylsulfinyl)allenes 1a,b under superelectrophilic activation.

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Published 22 Nov 2018

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