Copper(I) thiophen-2-carboxylate was successfully employed in the trimerization of [2.2.1] bicyclic vicbromotrimethyltin olefins (in their racemic composition), bearing different functionalities, to invariably obtain almost quantitative yields of the syn and anti tris-annelated benzenes. The two isomers come in different ratios, smaller than or equal to the statistical 1:3 ratio, depending on the steric hindrance opposed by the functionalities. In the case of enantiopure (3-bromo-4,7,7-trimethylbicyclo[2.2.1]hept-2- en-2-yl)trimethylstannane, the 1:9 ratio found with Cu(NO3)2·3H2O increases to 1:6.
Efficient cyclotrimerization of bicyclic vic-bromostannylalkenes promoted by copper(I) thiophen-2-carboxylate / Borsato, Giuseppe; De Lucchi, Ottorino; Fabris, Fabrizio; Groppo, Luca; Lucchini, Vittorio; Zambon, Alfonso. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 67:22(2002), pp. 7894-7897. [10.1021/jo020396s]
Efficient cyclotrimerization of bicyclic vic-bromostannylalkenes promoted by copper(I) thiophen-2-carboxylate
ZAMBON, Alfonso
2002
Abstract
Copper(I) thiophen-2-carboxylate was successfully employed in the trimerization of [2.2.1] bicyclic vicbromotrimethyltin olefins (in their racemic composition), bearing different functionalities, to invariably obtain almost quantitative yields of the syn and anti tris-annelated benzenes. The two isomers come in different ratios, smaller than or equal to the statistical 1:3 ratio, depending on the steric hindrance opposed by the functionalities. In the case of enantiopure (3-bromo-4,7,7-trimethylbicyclo[2.2.1]hept-2- en-2-yl)trimethylstannane, the 1:9 ratio found with Cu(NO3)2·3H2O increases to 1:6.
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