• Bulletin of the Korean Chemical Society
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• v.30 no.8
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• pp.1832-1834
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• 2009

A simple and safe method has been presented for conversion of olefins into bromohydrins using hydrogen bromide and hydrogen peroxide as bromide source by visible light induced within a very short time to get high yield bromohydrins along with a little mount dibromo-product. In this paper, cyclohexene is firstly carried out as the model substrate and investigated the bromination under HBr/$H_2O_2$ system using 150 W incandescent light irradiated in C$Cl_4$ within short time to get good yield of 2-bromocyclohexanol along with a little mount of 1,2-dibromocyclohexane; then, a series of alkenes are brominated to corresponding bromohydrins using the same protocol.

• Bulletin of the Korean Chemical Society
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• v.34 no.2
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• pp.500-504
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• 2013

In this paper, in addition to introducing efficient method for bromohydrin and bromoether preparation, simple, green and efficient method to C-N bond formation from alkene and N,N'-Dibromo-N,N'-1,2-ethanediyl-bis(p-toluenesulfonamide) [BNBTS] in water was investigated. The reaction between alkenes, ${\beta}$-cyclodexterin, and BNBTS took place in water afterward, by making media basic; it will give the corresponding valuable building blocks in good yields (45-79%).

• Applied Biological Chemistry
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• v.19 no.1
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• pp.1-23
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• 1976

The female moths of Lepidoptera comprising over 1,000,000 described species possess long-chain unsaturated alcohols or esters as the typical structure of potential sex attractants. In this experiment, various stereoisomers of $C_{16}-unsaturated$ acetates were synthesized for potential sex attractants; e.g., $CH_3(CH_2)_mCH=CH(CH_2)_nOR$ (m=0-12, n=1-13, R=H and $-COCH_3$). Seventeen acetates were spectrometrically examined so that the data would provide a ready catalog of gas chromatography and mass spectrometric data for comparison with natural insect sex attractants. Exclusively cis and trans isomers were obtained by the catalytic and chemical reduction methods, respectively. Commercially available $CH_3(CH_2)_mBr,\;CH_3(CH_2)_mC{\equiv}CH,\;HC{\equiv}C(CH_2)_nOH\;and\;HO(CH_2)_n\;OH$ were used for the synthetic starting material. 1-Alkynes, $CH_3(CH_2)_m\;C{\equiv}CH$ exceeding nine methylene groups did not condense with alkyl dihalides. The yield of coupling products was gradually decreased with increasing the molecular weight of diols. In the coupling reaction of $BrCH_2CH_2$ OTHP with acetylene gas, the tetrahydropyranyl ether of bromohydrin produced undesirable elimination product. In this experiment, it seems that p-toluenesulfonic acid is greatly favoured hydrolyzing agent over dilute sulfuric acid in the hydrolysis of the tetrahydropyranyl ether of long-chain alkynols.