Selenium dibromide as a mild brominating agent

Full text of DOI:10.1134/S1070363208070323

ISSN 1070-3632, Russian Journal of General Chemistry, 2008, Vol. 78, No. 7, p. 1463. © Pleiades Publishing, Ltd., 2008.
Original Russian Text © S.V. Amosova, E.V. Abramova, V.A. Potapov, 2008, published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 7, p. 1225.
LETTERS
TO THE EDITOR
Selenium Dibromide as a Mild Brominating Agent
S. V. Amosova, E. V. Abramova, and V. A. Potapov
Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
Received December 20, 2007
DOI: 10.1134/S1070363208070323
Various brominating agents are used in the modern
organic synthesis. The act differently than bromine and
allow a more selective bromination.
divinyl ether less selectively reacts with bromine, and
additional purification is needed to isolate the target
product.
1
Before our studies selenium dibromide has scarcely
been used in organic synthesis. We applied this reagent
in the synthesis of previously unknown 1-selena-4-
silafulvenes [1–3] by addition to diethinylsilanes. It
was found that selenium dibromide is a mild bromi-
nating agent which can be used in organic synthesis.
Bis(1,2-dibromoethyl) ether (I), mp 64–65°C. H
NMR spectrum (CCl4), δ, ppm: 3.90 m (4H, CH2),
6.06 m (2H, CH). 13C NMR spectrum (CCl4), δC, ppm:
32.40 (CH2), 82.90 (CH). Found, %: C 12.51, H 1.42,
Br 81.51. C4H6Br4O. Calculated, %: C 12.33; H 1.55;
Br 82.01.
The reaction of selenium dibromide with divinyl
ether (chloroform, –50°C) involves bromination of the
two double bonds to form bis(1,2-dibromoethyl) ether
(I) in 92% yield.
The NMR spectra were taken on a Bruker DPX-400
spectrometer (101.62 MHz for 13C, 400.13 MHz for
1H) against internal HMDS.
REFERENCES
2SeBr2
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O
Br
Br
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_50oC
Br
+ 2Se.
O
I
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The reaction proceeds highly selectively and gives
almost no by-products. Under the same conditions,
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