Herein, we report the first synthesis of chlorinated benzo[b]selenophenes via environmentally friendly electrophilic chlorocyclization reaction using “table salt” as a source of “electrophilic chlorine” and ethanol as a solvent. In addition, the synthesis of diverse halogenated heterocycles, including 3-chloro, 3-bromo and 3-iodo thiophenes, selenophenes, and benzo[b]selenophenes was successfully accomplished under the same environmentally benign reaction conditions. This methodology has several advantages over other previously reported reactions as it employs simple starting compounds, an environmentally friendly solvent, ethanol, and non-toxic inorganic reagents under mild reaction conditions, resulting in the high product yields.
This paper is the first report upon a somewhat extended series of investigations, started some two years ago, upon the drop weights, or surface tensions, of pure liquids, a t many temperatures. and their relationship to the values of that property in their binary or other admixtures in various proportions, at those temperatures The main object of the work is to provide such a further, perhaps more consistent, set of experimental data that eventually it may perhaps be possible to find the cause of the mutual effects of liquids upon one another; which, although absent in some cases, are great, and yet of widely dlflenng magnitude, in others. For some binary liquid mixtures it is known that the so-called luw of mixtures holds more or less rigidly, i. e., the value of a certain physical property of the mixture is equal to the slim of the values of that property for the pure constituents under like conditions, each multiplied by the ratio of its weight in the mixture, to the total weight of the system. Or, expressed as an equation, PMixt. = xP, + (Ix)Pb, where the terms
3 For the preparation of these inorganic compounds see the monograph by Price, "Per-acids and Their Salts," Longmans, Green and Co., London, 1912. 4 Ref. 3, p. 31. 5 See, in addition to the references given in Ref. 3, Palm, Z. anorg. Chem., 112, 697 (1920).
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