Cycloaddition reactions of 1,2-dehydro-o-carborane with thiophene, 2,5-dimethylthiophene, 2,5-dimethylfuran, [8](2,5)thiophenophane, and [8](2,5)furanophane are investigated. In all cases, except the reaction with the thiophenophane, both 4 + 2 and 2 + 2 cycloadducts are formed, with the 4 + 2 product dominating. The 4 + 2 adducts of the thiophenes are not stable but extrude sulfur under the reaction conditions to give "benzo-o-carboranes".
1997 organo-boron compounds, nonmetal heterocycles organo-boron compounds, nonmetal heterocycles S 0047 02 -148 Carboranophanes -(bridged by a single all-carbon chain or a carbon/sulfur bridge). -(BARNETT-THAMATTOOR, L.; WU, J. J.; HO, D. M.; JONES, M. JUN. ; Tetrahedron Lett. 37 (1996) 40, 7221-7224; Dep. Chem., Princeton Univ., Princeton, NJ 08544, USA; EN)
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