360768-64-5Relevant academic research and scientific papers
Facile synthesis of 7-dimethylamino-endo-tricyclo[5.2.2.01,6]undec-10-en-9-ones
Wu, Yao-Ting,Schirmer, Heiko,Noltemeyer, Mathias,De Meijere, Armin
, p. 2501 - 2506 (2001)
Pentacarbonyl[(2E)-3-cyclohexenyl-3-dimethylamino-1-ethoxy-2-propen-1- ylidene]chromium (2) yields 7-dimethylamino-endo-tricyclo[5.2.2.01,6]undec-10-en-9-ones 5 (15-88%, 12 examples) upon treatment with alkynes 3 in pyridine, most probably by a 6π-electrocyclization followed by a subsequent reductive elimination/intermolecular Diels-Alder reaction with the alkyne and eventual hydrolysis. The direct cyclization of 2 to the cyclohexane-annelated cyclopentadiene 6 is faster than the usual alkyne insertion of α,β-unsaturated Fischer carbene complexes. The [4+2] cycloadditions of 7 and the added alkynes 3 occur with high degrees of regio- and complete diastereoselectivity.
7-(Dimethylamino)tricyclo[5.2.2.01,6]undecene derivatives from β-cyclohexenyl β-dimethylamino-substituted α,β-unsaturated fischer carbenes
Wu, Yao-Ting,Labahn, Thomas,Demeter, Attila,Zachariasse, Klaas A.,De Meijere, Armin
, p. 4483 - 4491 (2007/10/03)
When heated in pyridine at 80°C, pentacarbonyl[(2E)-3-cyclohexenyl-3- (dimethylamino)-1-ethoxy-2-propen-1-yl-idene]chromium (1-Cr) and -tungsten (1-W) complexes undergo 6π-electrocyclization and subsequent reductive elimination to yield the cyclohexane-an
