Journal of the American Chemical Society, Vol.116, No.5, 1880-1889, 1994
Metallacycle Transfer from Zirconium to Main-Group Elements - A Versatile Synthesis of Heterocycles
The reaction of zirconium metallacycles is used to produce a variety of main group heterocycles including borole Diels-Alder dimers, galloles, indacyclopentadienes, siloles, germoles, stannoles, phospholes, arsoles, stiboles, bismoles, thiophenes, selenophenes, dihydrothiophenes, dihydroselenophenes, tetrahydrothiophenes, tetrahydroselenophenes, stannacyclopentanes, phospholenes, and isothiazoles. An X-ray crytallographic study of the borole Diels-Alder dimer of 1-phenyl-2,3,4,5-tetramethylborole is discussed and compared with the structure of 7-norbornenyl carbenium ions. The scope and potential for this metallacycle transfer reaction are delineated.
Keywords:METAL-PROMOTED CYCLIZATION;RAY CRYSTAL-STRUCTURE;ZIRCONOCENE COMPLEXES;ORGANIC-CHEMISTRY;SOLUTION BEHAVIOR;DIENES;DERIVATIVES;ALKENES;ENYNES;BICYCLIZATION