Selenium halide-induced bridge formation in [2.2]paracyclophanes

Abstract

SummaryAn addition/elimination sequence of selenium halides to pseudo-geminally bis(acetylene) substituted [2.2]paracyclophanes leads to new bridges with an endo-exo-diene substructure. The reactions have been found to be sensitive to the substitution of the ethynyl group. The formation of dienes with a zig-zag configuration is related to that observed for non-conjugated cyclic diynes of medium ring size.

Synthesis of 4-(4-Hydroxyaryl)-1,3-Dithiolium Perchlorates

“…Treatment of these perchlorates with a saturated NaHCO 3 solution gives the corresponding phenolates 4 as yellow crystalline products, which show mesoionic character [47,50] (scheme 2). The molecular structure of the new compounds was proved by analytical and spectral data (table 3) and by the following chemical transformation: treatment of an acetone suspension of the mesoionic compounds 4 with 70% perchloric acid regenerates the 1,3-dithiolium perchlorates 3 in quantitative yields (scheme 2).…”

Synthesis of 4-(2-Hydroxyaryl)-5-Methyl-1,3-Dithiol-2-Thiones

“…The discovery of highly conductive organic charge transfer complexes which are formed from tetrathiafulvalenes derivatives and the acceptor tetracyano-p-quinodimethane has prompted interest in the discovery of new electron donors and acceptors which exhibit similar conductivity. [1][2][3][4] In general, charge-transfer [5][6][7][8][9][10][11][12][13][14][15] or push-pull [16][17][18][19][20] compounds have significant applications in the field of conducting materials. For these reasons heterocyclic compounds -especially those containing sulfur and nitrogen -represent an important resource for the material chemistry [21][22][23][24] and also for medicinal chemistry.…”

Synthesis and Structural Characterization of Some 1,3-Dithiol-2-ylium Salts

“…Amongst these, sulfur and nitrogen-containing heterocycles receive a great deal of attention [6][7][8][9][10][11][12][13][14][15][16]. In the field of conducting materials charge-transfer [17][18][19][20][21][22] and push-pull [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38] compounds have important applications. 1,3-Dithiolium derivatives have been found to exhibit an excellent biological activity, especially against gram-positive and gram-negative bacteria [39].…”