Oxidation and halogenation of divinyl selenide. first synthesis of divinyl selenoxide


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Abstract

Efficient procedure was developed for the preparation of divinyl selenoxide in 92% yield by oxidation of divinyl selenide with sodium periodate. At the action of S-nucleophiles on the divinyl selenoxide it is reduced to divinyl selenide. The reaction of divinyl selenide with an equimolar amount of sulfuryl chloride or bromine led to halogenation products at the selenium atom: divinylselenium dichloride and divinylselenium dibromide. A rearrangement was discovered of divinylselenium dibromide into vinyl(1,2-dibromoethyl)-selenide. The hydrolysis of divinylselenium dichloride results in divinyl selenide.

About the authors

E. O. Kurkutov

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: amosova@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

V. A. Potapov

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Email: amosova@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

S. V. Amosova

Favorskii Irkutsk Institute of Chemistry, Siberian Branch

Author for correspondence.
Email: amosova@irioch.irk.ru
Russian Federation, ul. Favorskogo 1, Irkutsk, 664033

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