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18. In order to account for the regioselectivity observed in the
formation of 15 we speculate that this product derives
from a competing pathway involving nucleophilic attack
at the carbene by the electron rich acetylene 5. Electro-
cyclization of i leads to ii, which on purification results in
the isolation of the by-product 15. The inorganic chro-
mium complex (SÆCr(CO)5) generated in this sequence is
presumably also able to participate in a [2+2+1] reaction
with 5 affording the cyclopentadienone iii, which evidently
suffers reduction under the reaction conditions to cyclo-
pentenone 16.
The moderate yield observed in the key benzannulation
step (31%) presumably reflects the fine balance between
the desired transformation and a miriad of other possible
pathways in this case. For related group 6-mediated
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