By Desmurs J.-R., Gerard B., Goldstein M.J.
The natural molecules which are used, rather within the parts of pharmacy and agrochemicals, have gotten progressively more advanced either of their chemical nature and spacial configuration. a posh molecular constitution is necessarily fragile; it can't be produced lower than critical stipulations (in specific excessive strain and temperature). additionally there's a challenge of the scale-up of a product from the laboratory to the economic scale. The keep an eye on of the reactivity, selectivity, and yield and using sufficiently gentle commercial stipulations are all elements that has to be taken into consideration through commercial chemists. among the ''tools'' giving controllable reactivity, selectivity, and comparatively light response stipulations is bromine. The natural chemistry of bromine occasionally supplies unbelievable selectivities in comparison to these of chlorine. This quantity that's in line with ''Orgabrom '93'', brings jointly the most contributions provided at this occasion.
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Extra resources for Advances in Organobromine Chemistry II: Proceedings Orgabrom '93, Jerusalem, June 28-July 2, 1993
36). B T M A Br 3, aq N a O H R1--SO-R 2 R1--S--R 2 CHzC12 rt, or C1CH2CH2C1 reflux 47 - 98 % Fig. 28. Oxidation of sulfides to sulfoxides with BTMA Br 3 Although the oxidation of thiols with chlorine or bromine in the presence of water gives sulfonyl halides or sulfonic acids, the reaction of thiols with a stoichiometric amount of BTMA Br3 and sodium hydroxide in dichloromethanewater at room temperature gives disulfides in good yields (Fig. 29) (ref. 37). B T M A Br 3, aq N a O H 2 R--SH ~ CH2C12, rt, 10-20 min R--S--S--R 60-99 % Fig.
Recently, we also found that the reaction of primary amines and hydrazo compounds with BTMA Br 3 in aq. sodium hydroxide or in water gave corresponding nitriles and azo compounds in satisfactory yields, respectively (Fig. 27) (ref. 35). 5 - 10 h R-N-N-R 60-91% Fig. 27. Oxidation of primary amines and hydrazo compounds with BTMA Br3 43 Oxidation of sulfides to sulfoxides and oxidation of thiols to disulfides The oxidation of sulfides to sulfoxides are occasionally found to be unsatisfactory, since the resulting sulfoxides are easily oxidized to sulfones.
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