Chemistry - A European Journal
10.1002/chem.201702490
FULL PAPER
was filtered and the volatile components were removed under reduced
pressure to give the alkenyl bromide 15b. The crude was used in the
next step without further purification.
[9]
As expected considering Yamamoto’s work (reference [3k]) when a
reaction was performed with an alkynol similar to 2 but containing an
internal alkyne (1,1,6-triphenyl-5-hexyn-1-ol) we observed the formation
of the corresponding cyclopentyl ketone derivative [(2,2-
diphenylcyclopentyl)(phenyl)methanone]. We also performed an
experiment with the related enyne derivative 1,1,6-triphenyl-1-hexen-5-
yne, and in this case, we observed the formation of a complex mixture
of unidentified products.
Acknowledgements
We gratefully acknowledge financial support from MINECO-
Spain (grant CTQ2013-41336-P) and MEC (FPU-predoctoral
grant to P.A. and FPI-predoctoral grant to P.P.)
[10] Alkenyl fluorides are interesting compounds that have attracted more
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Fürstner, Chem. Eur. J. 2017, 23, 558-562; b) Y. Ye, T. Takada, S. L.
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Keywords: alkenyl halides • cyclization • halogens • synthesis
design • synthetic methods
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The reaction of alkynol 2a (1,1-diphenyl-5-hexyn-1-ol) in hexane (or
dichloromethane) with water-free hydrogen chloride (solution in diethyl
ether) led to the formation of the corresponding enyne derivative 1a
(
1,1-diphenyl-1-hexen-5-yne) through a dehydration reaction but we did
not observe the evolution of this compound to the desired cyclization
product 3a.
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