Synthesis of new functionalized organoselenium compounds by heterocyclization of selenium dihalides with pent-4-en-1-ol


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The reaction of selenium dihalides with pent-4-en-1-ol has been carried out for the first time. Efficient procedures for the synthesis of previously unknown bis(tetrahydrofuran-2-ylmethyl) selenide, dihalobis( tetrahydrofuran-2-ylmethyl)-λ4-selanes, and bis(tetrahydrofuran-2-ylmethyl) selenoxide have been developed on the basis of this reaction. The product structures have been studied by 1H, 13C, and 77Se NMR. Bis(tetrahydrofuran-2-ylmethyl) selenide and dihalobis(tetrahydrofuran-2-ylmethyl)-λ4-selanes represent equimolar mixtures of two diastereoisomers which display different signals in the 13C and 77Se NMR spectra. The oxidation of bis(tetrahydrofuran-2-ylmethyl) selenide with sodium periodate in methanol leads to the corresponding selenoxide consisting of 4 diastereoisomers.

作者简介

V. Potapov

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: amosova@irioch.irk.ru
俄罗斯联邦, ul. Favorskogo 1, Irkutsk, 664033

M. Musalov

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: amosova@irioch.irk.ru
俄罗斯联邦, ul. Favorskogo 1, Irkutsk, 664033

E. Kurkutov

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: amosova@irioch.irk.ru
俄罗斯联邦, ul. Favorskogo 1, Irkutsk, 664033

M. Musalova

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: amosova@irioch.irk.ru
俄罗斯联邦, ul. Favorskogo 1, Irkutsk, 664033

A. Albanov

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: amosova@irioch.irk.ru
俄罗斯联邦, ul. Favorskogo 1, Irkutsk, 664033

S. Amosova

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

编辑信件的主要联系方式.
Email: amosova@irioch.irk.ru
俄罗斯联邦, ul. Favorskogo 1, Irkutsk, 664033

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