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2005
Bridged compounds
Q 0060
7-(Dimethylamino)tricyclo[5.2.2.01,6]undecene Derivatives from β-Cyclohexenyl
α,β-Unsaturated Fischer Carbenes. — Ketones of
06- 078 β-Dimethylamino-Substituted
type (III) are the exclusive products derived from the title reaction of chromium complex (I) with alkynes (II). The enol ether moiety of primarily formed cyclohexane-anellated norbornadienes is hydrolyzed under the work-up conditions to give the norbornenone derivatives (III). Norbornene derivatives (V), derived from the reaction of
complex (I) with styrenes, do not undergo rapid subsequent hydrolysis. The formation
of bis-cycloadducts from suitable diynes largely depends upon the steric and electronic
properties of the corresponding alkynyl-substituted mono-cycloaddition product like
(VIII). — (WU, Y.-T.; LABAHN, T.; DEMETER, A.; ZACHARIASSE, K. A.; DE
MEIJERE*, A.; Eur. J. Org. Chem. 2004, 21, 4483-4491; Inst. Org. Biomol. Chem.,
Georg-August-Univ., D-37077 Goettingen, Germany; Eng.) — Klein
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