BIS(2-BROMOETHYL)SELENIUM DIBROMIDE AS THE SELENIUM-INTRODUCING REAGENT - ONE-POT PREPARATION OF 2,5-BIS(ALKOXYMETHYL)TETRAHYDROSELENOPHENES BY THE CYCLIZATION OF 1,5-HEXADIENE | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

1205013

Reference Type

Journal Article

Title

BIS(2-BROMOETHYL)SELENIUM DIBROMIDE AS THE SELENIUM-INTRODUCING REAGENT - ONE-POT PREPARATION OF 2,5-BIS(ALKOXYMETHYL)TETRAHYDROSELENOPHENES BY THE CYCLIZATION OF 1,5-HEXADIENE

Author(s)

Takanohashi, Y; Tabata, N; Tanase, T; Akabori, S

Year

1993

Is Peer Reviewed?

Yes

Journal

Journal of Organometallic Chemistry
ISSN: 0022-328X
EISSN: 1872-8561

Volume

450

Issue

1-2

Page Numbers

103-108

Web of Science Id

WOS:A1993LH77100016

Abstract

The reaction of bis(2-bromoethyl)selenium dibromide (1a)
with 1,5-hexadiene (2) in methanol or ethanol affords 2,5-bis(alkoxymethyl)
tetrahydroselenophene-1,1-dibromides (R = CH3 (3b), R = C2H5 (3c)) via 2,5-bis(bromomethyl)
tetrahydroselenophene-1,1-dibromide (3a). The reaction of 1a with 2 in 1-propanol, 2-methyl-1-
propanol or 1-butanol in the presence of sodium carbonate gave 2,5-bis(alkoXyMethyl)
tetrahydroselenophene (R = C3H7 (4a), R = (CH3)2CHCH2 (4b) and R = C4H9 (4c)) via 3a. The ratios
of the trans and cis isomers of 3a-3c are 3:2. In addition, the structure of trans-2,5-bis
(methoxymethyl)tetrahydroselenophene-1,1-dibromide (trans-3b) was determined by X-ray
crystallography.