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[1,3]/[1,4]-Sulfur atom migration in β-hydroxyalkylphosphine sulfides

Katarzyna Włodarczyk, Piotr Borowski and Marek Stankevič

Beilstein J. Org. Chem. 2020, 16, 88–105. https://doi.org/10.3762/bjoc.16.11

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Supporting Information File 1: Experimental procedures, compound characterization data, a mechanism for the rearrangement of 16 in the presence of Brønsted acid assessed by computational methods, and coordinates of computed compounds.
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Supporting Information File 2: Copies of NMR spectra of all pure compounds and their mixtures.
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[1,3]/[1,4]-Sulfur atom migration in β-hydroxyalkylphosphine sulfides

Katarzyna Włodarczyk, Piotr Borowski and Marek Stankevič

Beilstein J. Org. Chem. 2020, 16, 88–105. https://doi.org/10.3762/bjoc.16.11

How to Cite

Włodarczyk, K.; Borowski, P.; Stankevič, M. Beilstein J. Org. Chem. 2020, 16, 88–105. doi:10.3762/bjoc.16.11

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TY  - JOUR
A1  - Włodarczyk, Katarzyna
A1  - Borowski, Piotr
A1  - Stankevič, Marek
T1  - [1,3]/[1,4]-Sulfur atom migration in β-hydroxyalkylphosphine sulfides
JF  - Beilstein Journal of Organic Chemistry
PY  - 2020///
VL  - 16
SP  - 88
EP  - 105
SN  - 1860-5397
DO  - 10.3762/bjoc.16.11
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.16.11
KW  - Brønsted and Lewis acids
KW  - DFT
KW  - mechanistic studies
KW  - rearrangement
KW  - stereochemistry
KW  - sulfur atom migration
N2  - β-Hydroxyalkylphosphine sulfides undergo [1,3]- or [1,4]-sulfur atom phosphorus-to-carbon migration in the presence of Lewis or Brønsted acids. The direction of sulfur atom migration depends on the type of acid used for the reaction. In the presence of a Brønsted acid, mainly [1,3]-rearrangement is observed, whereas a Lewis acid catalyzes the [1,4]-sulfur migration. To gain insight into the mechanism of these transformations, the stereochemistry of these rearrangements have been tested, along with the conduction of some control experiments and DFT calculations.
ER  -

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Coxon, J. M. doi:10.1002/9781119716846.ch11
Tao, X.; Ni, S.; Kong, L.; Wang, Y.; Pan, Y. Radical boron migration of allylboronic esters. Chemical science 2022, 13, 1946–1950. doi:10.1039/d1sc06760e

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DUTTA AMIT KUMAR; KOTHA VENKATESH; CHANDRA DINESH; JAIN PRITESH; GURJAR BHAGWAN LAL; SAXENA ROHIT; MAHAJAN VISHAL A; BRAR GAGANPREET SINGH; KULYE MAHESH SAKHARAM; KLAUSENER ALEXANDER G M. FUSED BICYCLIC COMPOUNDS AND THEIR USE AS PEST CONTROL AGENTS. WO 2025202955 A1, Oct 2, 2025.

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